- One-pot synthesis of sulfonylhydrazones from sulfonyl chloride, hydrazine hydrate and vinyl azide in water
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A facile and eco-friendly protocol for the synthesis of sulfonylhydrazones from sulfonyl chlorides, hydrazine hydrate and vinyl azides was developed. The unique advantage of this approach is that desired products can be obtained efficiently in water, which meets the requirements of green chemistry and provides good perspectives for the sustainable production of new drug candidate. Also, this reaction proceeded in moderate to good yields with a wide tolerance of functional groups.
- Luo, Mengqiang,Wang, Hai,Ren, Xiaorong,Lu, Ruijuan,Qi, Chenze,Zhang, Yaohong,Shen, Runpu
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p. 2713 - 2722
(2021/03/19)
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- I2-Promoted [4 + 2] cycloaddition of: In situ generated azoalkenes with enaminones: Facile and efficient synthesis of 1,4-dihydropyridazines and pyridazines
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A facile and efficient strategy for the synthesis of 1,4-dihydropyridazines and pyridazines through I2-promoted [4 + 2] cycloaddition of in situ generated azoalkenes with enaminones has been developed. The switch in selectivity is attributed to the judici
- Baell, Jonathan B.,Feng, Jiajun,He, Tiantong,Huang, Fei,Xie, Yuxing,Yu, Yang
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supporting information
p. 9483 - 9493
(2020/12/15)
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- Sulfonylhydrazone derivative, and preparation method and application thereof
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The invention discloses a sulfonylhydrazone derivative, and a preparation method and application thereof. The preparation method comprises the following step of taking olefin azide and sulfonyl hydrazine as starting materials to carry out a reaction, wher
- -
-
Paragraph 0036; 0037; 0053-0055; 0056; 0057
(2020/01/03)
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- Pyrrolo-imidazo[1,2- A[pyridine Scaffolds through a Sequential Coupling of N-Tosylhydrazones with Imidazopyridines and Reductive Cadogan Annulation, Synthetic Scope, and Application
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A new strategy for the construction of 3-phenyl-1H-pyrrolo-imidazo[1,2-a]pyridine backbone is described. The reaction starts from the coupling between N-tosylhydrazones and 2-chloro-3-nitroimidazo[1,2-a]pyridines leading to the formation of 3-nitro-2-(ary
- Zhang, Kena,El Bouakher, Abderrahman,Levaique, Helene,Bignon, Jerome,Retailleau, Pascal,Alami, Mouad,Hamze, Abdallah
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p. 13807 - 13823
(2019/10/16)
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- Toward a Greener Barluenga-Valdés Cross-Coupling: Microwave-Promoted C-C Bond Formation with a Pd/PEG/H2O Recyclable Catalytic System
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A green Barluenga-Valdés cross-coupling reaction for the synthesis of 1,1-diarylethylenes using palladium catalysis has been developed. The new catalytic system based on Pd/Xphos-SO3Na or Pd/MeDavephos-CF3SO3 in PEG/H2O under microwave irradiation was found to be the best conditions for this transformation. The recyclability of the palladium catalyst system was also studied, and it was found to be active over nine runs without significant loss in its activity.
- Lamaa, Diana,Messe, Estelle,Gandon, Vincent,Alami, Mouad,Hamze, Abdallah
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supporting information
p. 8708 - 8712
(2019/11/03)
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- Copper(i)-catalyzed benzylation of triazolopyridine through direct C-H functionalization
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A general and efficient copper-catalyzed benzylation reaction of triazolopyridine with N-tosylhydrazones was developed. This reaction forms a C(sp2)-C(sp3) bond through cross-coupling, and represents an exceedingly practical method t
- Reddy Lonka, Madhava,Zhang, Jinquan,Gogula, Thirupathi,Zou, Hongbin
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p. 7455 - 7460
(2019/08/20)
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- Lewis Acid Catalyzed [4 + 2] Cycloaddition of N-Tosylhydrazones with ortho-Quinone Methides
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A formal [4 + 2] cycloaddition of N-tosylhydrazones with ortho-quinone methides was developed, affording the facile synthesis of diverse 1,3-oxazine derivatives under mild conditions. In this transformation, N-tosylhydrazones are used as a 1,2-dipole synt
- Wang, Chun-Ying,Han, Jia-Bin,Wang, Long,Tang, Xiang-Ying
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p. 14258 - 14269
(2019/11/11)
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- Synthesis of Multi-substituted Dihydropyrazoles by Copper-Mediated [4+1] Cycloaddition Reaction of N-Sulfonylhydrazones and Sulfoxonium Ylides
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A general and expeditious approach for the copper mediated synthesis of multi-functionalized dihydropyrazoles from N-sulfonylhydrazones and sulfoxonium ylides has been achieved under aerobic oxidative conditions. The formal [4+1] cycloaddition reaction ex
- Hu, Sipei,Du, Shiying,Yang, Zuguang,Ni, Lingfang,Chen, Zhengkai
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supporting information
p. 3124 - 3136
(2019/05/01)
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- One-pot cascade synthesis of pyrazole based isosteres of valdecoxib by a [3+2] cycloaddition sequence and evaluation of their cox inhibitory activity
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A series of 5-methyl-3,4-diaryl-substituted 1H-pyrazoles, N-isosteres of valdecoxib, was synthesized by a [3+2] cycloaddition/[1,5] sigmatropic rearrangement sequence starting from tosylhydrazine, aryl methyl ketones and terminal aryl alkynes bearing vari
- Roscales, Silvia,Bechmann, Nicole,Pietzsch, Jens,Kniess, Torsten
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p. 416 - 428
(2019/07/31)
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- Copper-catalyzed one-pot coupling reactions of aldehydes (ketones), tosylhydrazide and 2-amino(benzo)thiazoles: An efficient strategy for the synthesis of N-alkylated (benzo)thiazoles
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An efficient and practical C–N bond formation methodology for the synthesis of N-alkylated (benzo)thiazoles was developed, via the copper-catalyzed one-pot two-step reactions of 2-amino(benzo)thiazoles and aldehydes (ketones) with tosylhydrazide. This cross-coupling reaction proceeded smoothly and tolerated a broad range of functional groups (46 examples). A variety of functionalized N-alkylated (benzo)thiazoles were obtained in moderate to high yields. Notably, gram-scale synthesis of fanetizole (anti-inflammatory drug) was also realized through this protocol.
- Xie, Zengyang,Chen, Ruijiao,Ma, Mingfang,Kong, Lingdong,Liu, Jun,Wang, Cunde
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- Asymmetric Copper-Catalyzed C(sp)-H Bond Insertion of Carbenoids Derived from N-Tosylhydrazones
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A chiral copper(I)-phosphoramidite complex efficiently catalyzed the asymmetric insertion of the carbenoids derived from N-tosyl hydrazones into alkyne C-H bonds to give the corresponding chiral alkynylated products in up to 77% yield and with up to 74% e
- Osako, Takao,Nagaosa, Makoto,Hamasaka, Go,Uozumi, Yasuhiro
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supporting information
p. 2251 - 2256
(2018/10/20)
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- Copper-Catalyzed Dehydrogenative Diels-Alder Reaction
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A practical and effective copper-catalyzed dehydrogenative Diels-Alder reaction of gem-diesters and ketone with dienes has been established. The active dienophiles were generated in situ via a radical-based dehydrogenation process, which reacted with a wide variety of dienes to afford various polysubstituted cyclohexene derivatives in good to excellent yields.
- Jiang, Bing,Liang, Qiu-Ju,Han, Yu,Zhao, Meng,Xu, Yun-He,Loh, Teck-Peng
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supporting information
p. 3215 - 3219
(2018/06/11)
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- Selective Construction of 2-Substituted Benzothiazoles from o-Iodoaniline Derivatives S8 and N-Tosylhydrazones
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Selective construction of 2-substituted benzothiazoles from o-iodoaniline derivatives S8 and N-tosylhydrazone via a copper-promoted [3 + 1 + 1]-type cyclization reaction has been realized. In the protocol, the carbon atom on N-tosylhydrazone could be regulated to construct benzothiazole by changing the reaction system. Furthermore, the transformation has achieved the construction of multiple carbon-heteroatom bonds.
- Huang, Yubing,Zhou, Peiqi,Wu, Wanqing,Jiang, Huanfeng
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p. 2460 - 2466
(2018/02/23)
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- Cooperative Iodide Pd(0)-Catalysed Coupling of Alkoxyallenes and N-Tosylhydrazones: A Selective Synthesis of Conjugated and Skipped Dienes
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Palladium(0)-catalysed hydro-alkylation or -alkenylation of alkoxyallenes with N-tosylhydrazones gives direct access to conjugated and skipped 1-alkoxydienes with high efficiency and excellent functional-group compatibility. The reaction is proposed to in
- Parisotto, Stefano,Palagi, Lorenzo,Prandi, Cristina,Deagostino, Annamaria
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supporting information
p. 5484 - 5488
(2018/03/27)
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- N-Tosylhydrazone directed annulation via C-H/N-N bond activation in Ru(ii)/PEG-400 as homogeneous recyclable catalytic system: a green synthesis of isoquinolines
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A green and sustainable methodology for the synthesis of isoquinolines using Ru(ii)/PEG-400 as a homogeneous recyclable catalytic system has been demonstrated. N-Tosylhydrazone, a rarely explored directing group, has been successfully employed for an annu
- Deshmukh, Dewal S.,Bhanage, Bhalchandra M.
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supporting information
p. 4864 - 4873
(2018/07/15)
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- Rhodium-Catalyzed B-H Bond Insertion Reactions of Unstabilized Diazo Compounds Generated in Situ from Tosylhydrazones
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Although transition-metal-catalyzed B-H bond insertion of carbenes into stable borane adducts has emerged as a promising method for organoborane synthesis, all the diazo compounds used to date as carbene precursors have had an electron-withdrawing group to stabilize them. Herein, we report a protocol for rhodium-catalyzed B-H bond insertion reactions of unstabilized diazo compounds generated in situ from tosylhydrazones. In addition, by using chiral dirhodium catalysts, we also achieved an asymmetric version of the reaction with good to excellent enantioselectivities (up to 98:2 e.r.). This is the first enantioselective heteroatom-hydrogen bond insertion reaction to use unstabilized diazo compounds as carbene precursors. The protocol exhibited good functional group tolerance and could be carried out on a gram scale. It also enabled one-pot transformation of a carbonyl group to a boryl group enantioselectively. The B-H bond insertion products could be easily transformed into chiral alcohols and other widely used organoboron reagents with enantiomeric fidelity.
- Pang, Yue,He, Qiao,Li, Zi-Qi,Yang, Ji-Min,Yu, Jin-Han,Zhu, Shou-Fei,Zhou, Qi-Lin
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supporting information
p. 10663 - 10668
(2018/09/06)
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- Zinc-promoted cyclization of tosylhydrazones and 2-(dimethylamino)malononitrile: An efficient strategy for the synthesis of substituted 1-tosyl-1: H -pyrazoles
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A Zn(OTf)2-promoted cyclization reaction of tosylhydrazones with 2-(dimethylamino)malononitrile has been successfully developed providing an efficient strategy for the synthesis of substituted 1-tosyl-1H-pyrazoles.
- Zhang, Bang-Hong,Lei, Lin-Sheng,Liu, Si-Zhan,Mou, Xue-Qing,Liu, Wei-Ting,Wang, Shao-Hua,Wang, Jie,Bao, Wen,Zhang, Kun
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supporting information
p. 8545 - 8548
(2017/08/04)
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- Copper-Catalyzed Cyanation of N-Tosylhydrazones with Thiocyanate Salt as the "cN" Source
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A novel protocol for the synthesis of α-aryl nitriles has been successfully achieved via a copper-catalyzed cyanation of N-tosylhydrazones employing thiocyanate as the source of cyanide. The features of this method include a convenient operation, readily available substrates, low-toxicity thiocyanate salts, and a broad substrate scope.
- Huang, Yubing,Yu, Yue,Zhu, Zhongzhi,Zhu, Chuanle,Cen, Jinghe,Li, Xianwei,Wu, Wanqing,Jiang, Huanfeng
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p. 7621 - 7627
(2017/07/26)
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- Copper catalysed alkylation of heteroaryl chloride via migratory insertion of carbenes
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Cross-coupling reaction involving Cu catalysed carbene migratory insertion with N-tosylhydrazones as the reaction partner with various substituted cyanuric chloride were studied, which has been recognized as a new type of cross-coupling reaction. Cu-carbe
- Mudaliar, Sulochana S.,Zala, Shailesh N.,Chikhalia, Kishor H.
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supporting information
p. 142 - 148
(2017/08/08)
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- Hydrohydrazination of Arylalkynes Catalyzed by an Expanded Ring N-Heterocyclic Carbene (er-NHC) Gold Complex under Solvent-Free Conditions
-
[(THD-Dipp)AuOTf], supported by the strongly electron donating, sterically bulky THD-Dipp (1,3-bis(2,6-diisopropylphenyl)hexahydro-2H-1,3-diazepine-2-ylidene) seven-membered N-heterocyclic carbene ligand, efficiently promotes intermolecular addition of Ts- and Boc-hydrazine to arylalkynes under solvent-free conditions.
- Morozov, Oleg S.,Gribanov, Pavel S.,Asachenko, Andrey F.,Dorovatovskii, Pavel V.,Khrustalev, Victor N.,Rybakov, Viktor B.,Nechaev, Mikhail S.
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supporting information
p. 1463 - 1468
(2016/05/19)
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- Copper-Mediated [3 + 2] Oxidative Cyclization Reaction of N-Tosylhydrazones and β-Ketoesters: Synthesis of 2,3,5-Trisubstituted Furans
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The first attempt at utilizing N-tosylhydrazones as two-carbon synthons has been successfully achieved, which underwent a copper-mediated [3 + 2] oxidative cyclization reaction to afford 2,3,5-trisubstituted furans in moderate to good yields. The features of this method include inexpensive metal catalyst, readily available substrates, high regioselectivity, and convenient operation. The studies provide important approaches for further exploration of the powerful and diverse reaction abilities of N-tosylhydrazones.
- Huang, Yubing,Li, Xianwei,Yu, Yue,Zhu, Chuanle,Wu, Wanqing,Jiang, Huanfeng
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p. 5014 - 5020
(2016/07/06)
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- Copper-Catalyzed Reductive N-Alkylation of Amides with N-Tosylhydrazones Derived from Ketones
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A CuI-catalyzed reductive coupling of ketone-derived N-tosylhydrazones with amides is presented. Under the optimized conditions, an array of N-tosylhydrazones derived from aryl–alkyl and diaryl ketones could couple effectively with a wide variety of (hete
- Xu, Peng,Qi, Fu-Ling,Han, Fu-She,Wang, Yan-Hua
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supporting information
p. 2030 - 2034
(2016/07/28)
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- I2-TBHP-catalyzed oxidative cross-coupling of N -sulfonyl hydrazones and isocyanides to 5-aminopyrazoles
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I2-TBHP-catalyzed oxidative cross coupling of N-sulfonyl hydrazones with isocyanides has been realized for the synthesis of 5-aminopyrazoles through formal [4 + 1] annulation via in situ azoalkene formation. Notable features are the metal/alkyn
- Senadi, Gopal Chandru,Hu, Wan-Ping,Lu, Ting-Yi,Garkhedkar, Amol Milind,Vandavasi, Jaya Kishore,Wang, Jeh-Jeng
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supporting information
p. 1521 - 1524
(2015/03/30)
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- Copper-catalyzed radical reaction of N -tosylhydrazones: Stereoselective synthesis of (E)-vinyl sulfones
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A new chemistry of hydrazines that is a copper-catalyzed radical reaction to synthesize vinyl sulfones from readily available N-tosylhydrazones has been described. The protocol provides a novel strategy for the synthesis of various vinyl sulfones including α, β-disubstituted ones and terminal ones. The advantages of the transformation include excellent E stereoselectivity, broad substrate scope, low cost of reagents, and convenient operation. A novel and efficient one-pot synthesis of alkynes from N-tosylhydrazones has been achieved. The studies provide important complementary approaches for the syntheses of vinyl sulfones and alkynes.
- Mao, Shuai,Gao, Ya-Ru,Zhu, Xue-Qing,Guo, Dong-Dong,Wang, Yong-Qiang
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supporting information
p. 1692 - 1695
(2015/04/14)
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- Copper(I)-Catalyzed Alkylation of Polyfluoroarenes through Direct C - H Bond Functionalization
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The copper(I)-catalyzed alkylation of electron-deficient polyfluoroarenes with N-tosylhydrazones and diazo compounds has been developed. This reaction uses readily available starting materials and is operationally simple, thus representing a practical method for the construction of C(sp2) - C(sp3) bonds with polyfluoroarenes through direct C - H bond functionalization. Mechanistically, copper(I) carbene formation and subsequent migratory insertion are proposed as the key steps in the reaction pathway.
- Xu, Shuai,Wu, Guojiao,Ye, Fei,Wang, Xi,Li, Huan,Zhao, Xia,Zhang, Yan,Wang, Jianbo
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supporting information
p. 4669 - 4672
(2015/04/14)
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- Regioselective Synthesis of Vinyl Halides, Vinyl Sulfones, and Alkynes: A Tandem Intermolecular Nucleophilic and Electrophilic Vinylation of Tosylhydrazones
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A diazo species is trapped in an intermolecular fashion by two independent ion species in tandem at the carbene center to install an electrophile and a nucleophile on the same carbon. This metal-free concept, which is unprecedented, has been illustrated by regioselective synthesis of a variety of vinyl halides, vinyl sulfones, and alkyne derivatives. (Chemical Equation Presented).
- Ojha, Devi Prasan,Prabhu, Kandikere Ramaiah
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supporting information
p. 18 - 21
(2015/07/28)
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- Pd-Catalyzed Highly Regio- and Stereoselective Formation of C-C Double Bonds: An Efficient Method for the Synthesis of Benzofuran-, Dihydrobenzofuran-, and Indoline-Containing Alkenes
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A highly regio- and stereoselective C-C double bond formation reaction via Pd-catalyzed Heck-type cascade process with N-tosylhydrazones has been developed. Various N-tosylhydrazones derived from both ketones and aldehydes are found to be efficient substrates to provide di- and trisubstituted olefins with high regio- and stereoselectivity. Furthermore, this reaction has a good functional group tolerance and different benzofuran-, dihydrobenzofuran-, and indoline-containing alkene products were obtained with high selectivity.
- Gao, Yang,Xiong, Wenfang,Chen, Huoji,Wu, Wanqing,Peng, Jianwen,Gao, Yinglan,Jiang, Huanfeng
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p. 7456 - 7467
(2015/08/18)
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- A direct facile and effective synthesis of various 1,1-heterodiaryl alkenes through Pd catalyzed cross coupling reaction using N-tosylhydrazones via C-OH bond activation
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At this event for the first time, the direct arylation with the generation of a facile and effective process for the synthesis of alkenes has been established through in situ C-OH activation afterward Pd catalyzed C-C bond formation of heteroarenols with
- Patel, Poojan K.,Dalvadi, Jignesh P.,Chikhalia, Kishor H.
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supporting information
p. 6585 - 6589
(2015/11/09)
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- Rhodium(III)-catalyzed ortho alkenylation of n-phenoxyacetamides with n-tosylhydrazones or diazoesters through C-H activation
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A coupling reaction of N-phenoxyacetamides with N-tosylhydrazones or diazoesters through RhIII-catalyzed C-H activation is reported. In this reaction, ortho-alkenyl phenols were obtained in good yields and with excellent regio- and stereoselectivity. Rh-c
- Hu, Fangdong,Xia, Ying,Ye, Fei,Liu, Zhenxing,Ma, Chen,Zhang, Yan,Wang, Jianbo
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supporting information
p. 1364 - 1367
(2014/03/21)
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- Facile one-pot synthesis of N-alkylated benzimidazole and benzotriazole from carbonyl compounds
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An efficient one-pot N-alkylation of benzimidazole and benzotriazole from carbonyl compounds and tosylhydrazide has been accomplished via copper powder-catalyzed N - H bond insertion affording N-alkylated products in good yields. The reaction can tolerate a wide range of carbonyl compounds, such as aryl, alkyl, heterocyclic and α,β-unsaturated ketones, and aldehydes.
- Meng, Xu,Li, Xiaolong,Chen, Wenlin,Zhang, Yuanqing,Wang, Wen,Chen, Jinying,Song, Jinli,Feng, Huijie,Chen, Baohua
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p. 349 - 356
(2014/04/17)
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- I2/TBPB mediated oxidative reaction of N-tosylhydrazones with anilines: Practical construction of 1,4-disubstituted 1,2,3-triazoles under metal-free and azide-free conditions
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An efficient I2 (20 mol %)/TBPB mediated oxidative formal [4 + 1] cycloaddition of N-tosylhydrazones with anilines via C-N/N-N bond formation and S-N cleavage has been developed. This protocol represents a simple, general, and efficient approac
- Cai, Zhong-Jian,Lu, Xin-Mou,Zi, You,Yang, Chao,Shen, Ling-Jie,Li, Jian,Wang, Shun-Yi,Ji, Shun-Jun
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supporting information
p. 5108 - 5111
(2014/12/11)
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- Copper-catalyzed aerobic oxidative transformation of ketone- Derived N-tosyl hydrazones: An entry to alkynes
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A novel strategy involving Cu-catalyzed oxidative transformation of ketone-derived hydrazone moiety to various synthetic valuable internal alkynes and diynes has been developed. This method features inexpensive metal catalyst, green oxidant, good functional group tolerance, high regioselectivity and readily available starting materials. Oxidative deprotonation reactions were carried out to form internal alkynes and symmetrical diynes. Cross-coupling reactions of hydrazones with halides and terminal alkynes were performed to afford functionalized alkynes and unsymmetrical conjugated diynes. A mechanism proceeding through a Cu-carbene intermediate is proposed for the CC triple bond formation.
- Li, Xianwei,Liu, Xiaohang,Chen, Huoji,Wu, Wanqing,Qi, Chaorong,Jiang, Huanfeng
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supporting information
p. 14485 - 14489
(2015/02/05)
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- Reductive coupling reactions: A new strategy for C(sp3)-P bond formation
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The C(sp3)-P bond forming reaction utilizing N-tosylhydrazones as readily available alkylating reagents was developed, which provides a new opportunity for preparing phosphine oxide derivatives with moderate to good yields. This reductive coupling reaction is proposed to proceed through an insertion of copper carbene into P-H bond of H-phosphorus oxides. The salient features of the reaction are operational simplicity and functional-group tolerance.
- Chen, Zi-Sheng,Zhou, Zhao-Zhao,Hua, Hui-Liang,Duan, Xin-Hua,Luo, Jian-Yi,Wang, Jia,Zhou, Ping-Xin,Liang, Yong-Min
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supporting information
p. 1065 - 1068
(2013/02/25)
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- An easy access to fluoroalkanes by deoxygenative hydrofluorination of carbonyl compounds via their tosylhydrazones
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An efficient and operationally simple synthesis of fluoroalkanes by deoxygenative hydrofluorination of carbonyl compounds via their tosylhydrazone surrogates is reported. The reaction can be carried out in a one-pot procedure directly from carbonyl compounds.
- Yadav, Arvind K.,Srivastava, Vishnu P.,Yadav, Lal Dhar S.
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supporting information
p. 2154 - 2156
(2013/03/14)
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- Palladium-catalyzed oxidative cross-coupling of N-tosylhydrazones with indoles: Synthesis of N-vinylindoles
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A general and efficient palladium-catalyzed oxidative cross-coupling reaction of N-tosylhydrazones with indoles providing N-vinylindoles has been developed. The reaction proceeds smoothly with various indoles and N-tosylhydrazones in a stereocontrolled ma
- Zeng, Xiaobao,Cheng, Guolin,Shen, Jinhai,Cui, Xiuling
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supporting information
p. 3022 - 3025
(2013/07/26)
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- Copper acetoacetonate [Cu(acac)2]/BINAP-promoted Csp 3-N bond formation via reductive coupling of N-tosylhydrazones with anilines
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We report the the copper(II) acetoacetonate [Cu(acac)2]/BINAP- catalyzed synthesis of arylamines from N-tosylhydrazones and anilines. A fine tuning of the reaction conditions was required to accomplish the cross-coupling successfully, including the ligands effect and the addition of small amounts of water. The characteristic feature of this protocol is its functional group compatibility and its chemoselectivity when various aminophenol derivatives were used. Taking into consideration the interest for this copper-reductive coupling in which no stoichiometric metal hydride reagent is employed, this can be considered as an alternative to the conventional reductive amination.
- Aziz, Jessy,Brion, Jean-Daniel,Hamze, Abdallah,Alami, Mouad
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supporting information
p. 2417 - 2429
(2013/10/01)
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- Copper-mediated synthesis of 1,2,3-triazoles from N-tosylhydrazones and anilines
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NNNifty targets: In a straightforward copper-mediated synthesis of 1,4-disubstituted and 1,4,5-trisubstituted 1,2,3-triazoles, readily available aniline and N-tosylhydrazone substrates underwent cyclization through Ci£N and Ni£N bond formation (see scheme
- Chen, Zhengkai,Yan, Qiangqiang,Liu, Zhanxiang,Xu, Yiming,Zhang, Yuhong
-
supporting information
p. 13324 - 13328
(2014/01/06)
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- Transition-metal-free synthesis of pinacol alkylboronates from tosylhydrazones
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Highly efficient: Pinacol alkylboronates were synthesized by the reaction of tosylhydrazones with bis(pinacolato)diboron or pinacolborane under transition-metal-free conditions. This reaction represents an expeditious conversion of carbonyl functionality into a boronate group. Copyright
- Li, Huan,Wang, Long,Zhang, Yan,Wang, Jianbo
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supporting information; experimental part
p. 2943 - 2946
(2012/04/18)
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- Reductive azidation of carbonyl compounds via tosylhydrazone intermediates using sodium azide
-
Simple and direct: Aldehydes and ketones can be transformed into alkyl azides through a reductive coupling of the corresponding tosylhydrazones in a process that takes place simply in the presence of K2CO3, tetrabutylammonium bromide
- Barluenga, Jose,Tomas-Gamasa, Maria,Valdes, Carlos
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supporting information; experimental part
p. 5950 - 5952
(2012/07/03)
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- Carbon-carbon bond formation: Palladium-catalyzed oxidative cross-coupling of N-tosylhydrazones with allylic alcohols
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In the zone: Pd-catalyzed oxidative cross-coupling of N-tosylhydrazones with allylic alcohols leads to C-C bond formation. A palladium-carbene migratory insertion is proposed to play the key role in this transformation. The reaction proceeds with readily available starting materials to afford substituted alkenes in a highly stereoselective manner (see scheme). Copyright
- Chen, Huoji,Huang, Li,Fu, Wei,Liu, Xiaohang,Jiang, Huanfeng
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p. 10497 - 10500
(2012/11/06)
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- Coupling of n-tosylhydrazones with terminal alkynes catalyzed by copper(i): Synthesis of trisubstituted allenes
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The easy way to allenes: An operationally simple reaction under mild conditions has led to the direct formation of trisubstituted allenes (see scheme; Ts=4-toluenesulfonyl). An unprecedented copper-carbene migratory insertion process seems to take place,
- Xiao, Qing,Xia, Ying,Li, Huan,Zhang, Yan,Wang, Jianbo
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supporting information; experimental part
p. 1114 - 1117
(2011/04/16)
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- Copper-catalyzed direct benzylation or allylation of 1,3-azoles with N -tosylhydrazones
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Cu-Catalyzed cross-coupling of N-tosylhydrazones with 1,3-azoles leads to the direct C-H benzylation or allylation. Cu carbene migratory insertion is proposed to play the key role in this transformation.
- Zhao, Xia,Wu, Guojiao,Zhang, Yan,Wang, Jianbo
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supporting information; experimental part
p. 3296 - 3299
(2011/04/24)
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- Palladium-catalyzed oxidative cross-coupling of N-tosylhydrazones or diazoesters with terminal alkynes: A route to conjugated enynes
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Coming at them from another angle: In a fresh approach to the synthesis of conjugated alkynes, the palladium-catalyzed cross-coupling of N-tosylhydrazones or diazoesters with terminal alkynes provided the desired enyne products with excellent stereoselectivity (see scheme; Ts=p-toluenesulfonyl). The reaction is proposed to involve an unprecedented alkynyl migratory insertion of a palladium carbene complex. Copyright
- Zhou, Lei,Ye, Fei,Ma, Jiachen,Zhang, Yan,Wang, Jianbo
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supporting information; experimental part
p. 3510 - 3514
(2011/05/12)
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- Pd-catalyzed oxidative cross-coupling of N-tosylhydrazones with arylboronic acids
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The Pd-catalyzed reaction of N-tosylhydrazones and arylboronic acids provides olefin derivatives. This oxidative cross-coupling is suggested to proceed through a migratory insertion process of a Pd carbene intermediate.
- Zhao, Xia,Jing, Jing,Lu, Kui,Zhang, Yan,Wang, Jianbo
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supporting information; experimental part
p. 1724 - 1726
(2010/07/06)
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- Straightforward synthesis of ethers: Metal-free reductive coupling of tosylhydrazones with alcohols or Phenols
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(Figure Presented) Ethers made easy: Heating a solution containing a tosylhydrazone and either a phenol or an alcohol in the presence of K 2CO3 leads to the corresponding ethers (see scheme; MW=microwave, Ts=tosyl). The reaction is fairly general for the preparation of aryl alkyl and alkyl alkyl ethers, and represents a new method for the reductive etherification of carbonyl compounds.
- Barluenga, Jose,Tomas-Gamasa, Maria,Aznar, Fernando,Valde, Carlos
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supporting information; experimental part
p. 4993 - 4996
(2010/09/08)
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- Copper-catalyzed nitrogen loss of sulfonylhydrazones: A reductive strategy for the synthesis of sulfones from carbonyl compounds
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Figure Presented. An efficient method for the synthesis of sulfones via nitrogen loss of sulfonyl hydrazones is described. The reaction was performed in the presence of simple copper salt and base by utilization of sulfonyl hydrazones, which were easily p
- Feng, Xing-Wen,Wang, Jian,Zhang, Ji,Yang, Jing,Wang, Na,Yu, Xiao-Qi
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supporting information; experimental part
p. 4408 - 4411
(2010/12/19)
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