- 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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- Pd-Catalyzed Coupling of Thioamides with N-Tosylhydrazones/Trapping by Esters Cascade Reaction
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N,N-Disubstituted thioamides coupled with N-tosylhydrazones under Pd(TFA)2/tBuXPhos catalyst and NaOtBu, and the intermediates from palladium carbene migratory insertion containing β-hydrogen were trapped by intramolecular esters activated by BF3·Et2O ins
- Cai, Zhongliang,Yao, Zhi,Jiang, Liqin
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supporting information
p. 311 - 316
(2021/01/26)
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- Copper(I)/Bpy-Catalyzed C-2-H Benzylation of Quinazolin-4(3H)-ones with N-Tosylhydrazones
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A general and efficient copper-catalyzed C–H benzylation reaction of quinazolin-4(3H)-ones with N-tosylhydrazones is reported. The formation of new C(sp3)–C(sp2) bonds through cross-coupling occurs at the electron-poor C-2 position of quinazolin-4(3H)-one and represents an exceedingly practical method to afford 2-benzylated quinazolin-4(3H)-ones in moderate to good yields under mild reaction conditions. A possible reaction mechanism for this transformation was proposed. This catalytic transformation has the potential to be an important synthetic application for the late-stage functionalization of advanced synthetic intermediates.
- Li, Fei,Gu, Xiao-Juan,Zeng, Chang-E.,Li, Xia,Liu, Bo,Huang, Guo-Li
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p. 2923 - 2928
(2020/05/16)
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- Umpolung Difunctionalization of Carbonyls via Visible-Light Photoredox Catalytic Radical-Carbanion Relay
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The combination of photoredox catalysis with the Wolff-Kishner (WK) reaction allows the difunctionalization of carbonyl groups by a radical-carbanion relay sequence (photo-Wolff-Kishner reaction). Photoredox initiated radical addition to N-sulfonylhydrazones yields α-functionalized carbanions following the WK-type mechanism. With sulfur-centered radicals, the carbanions are further functionalized by reaction with electrophiles including CO2 and aldehydes, whereas CF3 radical addition furnishes a wide range of gem-difluoroalkenes through β-fluoride elimination of the generated α-CF3 carbanions. More than 80 substrate examples demonstrate the broad applicability of this reaction sequence. A series of investigations including radical inhibition, deuterium labeling, fluorescence quenching, cyclic voltammetry, and control experiments support the proposed radical-carbanion relay mechanism.
- Wang, Shun,Cheng, Bei-Yi,Sr?en, Matea,K?nig, Burkhard
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supporting information
p. 7524 - 7531
(2020/08/05)
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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
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Paragraph 0036; 0037; 0053-0055; 0056; 0057
(2020/01/03)
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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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- 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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- 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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- Palladium-catalyzed heck-type cascade cyclization of (Z)-1-iodo-1,6-dienes with N-tosyl hydrazones
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A palladium-catalyzed heck-type cascade cyclization of (Z)-1-iodo-1,6-dienes with N-tosyl hydrazones is reported. The alkylpalladium intermediate coupled with the diazo compound, generating the second alkylpalladium species bearing two β-H, which generate
- Li, Jun,Chi, Xiaochen,Meng, Long,Jiao, Luyang,Shang, Wenhui,Wang, Ping,Zhang, Daopeng,Dong, Yunhui,Liu, Qing,Liu, Hui
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supporting information
p. 7356 - 7360
(2018/10/24)
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- Multi-component one-pot reaction of aromatic carbonyl compounds, tosylhydrazide, and arylboronic acids
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In this paper, we developed a new method using 4-bromoacetophenone as the starting material, with tosylhydrazide and two arylboronic acids using Barluenga and Suzuki couplings in a four-component one-pot reaction to afford the target product 4-benzyl-1,1-biphenyls. This system that we have developed enables the use of easily accessible starting materials and can be employed on a wide variety of substrates with good functional group tolerance. In particular, this protocol can be applied to the synthesis of 4-(1-([1,1-biphenyl]-4-yl)ethyl)pyridine derivatives, a class of potential analogs of CPY17 inhibitors of prostate cancer.
- Gu, Ningning,Wei, Yu,Liu, Ping,Liu, Yan,Dai, Bin
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- The microwave-assisted ortho-alkylation of azine N-oxides with N-tosylhydrazones catalyzed by copper(i) iodide
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A copper catalyzed regioselective cross-coupling of N-tosylhydrazones with azine N-oxides to yield ortho-alkylated products in moderate to good yields is reported. The reaction is facilitated by microwave, takes place without any ligand, and uses inexpensive copper(i) iodide as the catalyst.
- Jha, Abadh Kishor,Jain, Nidhi
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p. 1831 - 1834
(2016/02/05)
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- One-step synthesis of sulfonamides from N-tosylhydrazones
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The first described reaction between N-tosylhydrazone and SO2 is reported to provide alkyl sulfonamides in the presence of various amines. In this procedurally simple method, hydrazones of both unsaturated aldehydes and ketones proceed in moder
- Tsai, Andy S.,Curto, John M.,Rocke, Benjamin N.,Dechert-Schmitt, Anne-Marie R.,Ingle, Gajendrasingh K.,Mascitti, Vincent
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supporting information
p. 508 - 511
(2016/02/18)
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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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- Base-promoted coupling of carbon dioxide, amines, and N-tosylhydrazones: A novel and versatile approach to carbamates
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A base-promoted three-component coupling of carbon dioxide, amines, and N-tosylhydrazones has been developed. The reaction is suggested to proceed via a carbocation intermediate and constitutes an efficient and versatile approach for the synthesis of a wide range of organic carbamates. The advantages of this method include the use of readily available substrates, excellent functional group tolerance, wide substrate scope, and a facile work-up procedure.
- Xiong, Wenfang,Qi, Chaorong,He, Haitao,Ouyang, Lu,Zhang, Min,Jiang, Huanfeng
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p. 3084 - 3087
(2015/05/12)
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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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- 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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- An unprecedented approach to the Gabriel amine synthesis utilizing tosylhydrazones as alkylating agents
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A new and one-pot version of the Gabriel phthalimide amine synthesis utilizing carbonyl compounds as alkylating agents via their tosylhydrazone surrogates is disclosed. The alkylation involves copper catalysed carbene insertion into the N-H bond of phthalimide. Basically, the protocol also offers a powerful tool for deoxygenative hydroamination of carbonyl compounds.
- Yadav, Arvind K.,Yadav, Lal Dhar S.
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p. 34764 - 34767
(2014/11/08)
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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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- Copper-catalyzed direct ortho-alkylation of N-iminopyridinium ylides with N-tosylhydrazones
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Copper-catalyzed cross-coupling of N-tosylhydrazones with N-iminopyridinium ylides leads to the direct C-H alkylation. This direct C-H bond alkylation transformation uses inexpensive CuI as the catalyst without any ligand. The reaction is operationally simple and conducted under mild conditions, giving the corresponding alkylated pyridines in moderate to good yields. DFT calculation provides insights into the reaction mechanism, suggesting that the reaction proceeds through the Cu carbene migratory insertion process.
- Xiao, Qing,Ling, Lin,Ye, Fei,Tan, Renchang,Tian, Leiming,Zhang, Yan,Li, Yuxue,Wang, Jianbo
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supporting information
p. 3879 - 3885
(2013/05/22)
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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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- One-pot synthesis of S-alkyl dithiocarbamates via the reaction of N-tosylhydrazones, carbon disulfide and amines
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A new, convenient and efficient transition metal-free synthesis of S-alkyl dithiocarbamates through one-pot reaction of N-tosylhydrazones, carbon disulfide and amines is reported. Tosylhydrazones derived from various aromatic and aliphatic ketones or aldehydes were tested and gave dithiocarbamates in good to excellent yields. The tosylhydrazones can be generated in situ without isolation, which provides a simpler one-pot method to synthesize dithiocarbamates via the reaction of carbonyl compounds, carbon disulfide and amines in the presence of 4-methylbenzenesulfonohydrazide.
- Sha, Qiang,Wei, Yun-Yang
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supporting information
p. 5615 - 5620
(2013/09/12)
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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
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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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- 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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