- Stereodivergent Synthesis of Tertiary Fluoride-Tethered Allenes via Copper and Palladium Dual Catalysis
-
Herein we describe a protocol for the unprecedented stereodivergent synthesis of tertiary fluoride-tethered allenes bearing a stereogenic center and stereogenic axis via Cu/Pd synergistic catalysis. A broad scope of conjugated enynes are coupled with various α-fluoroesters in high yields with high diastereoselectivities and generally >99% ee. In addition, the four stereoisomers of the allene products ensure precise access to the corresponding four stereoisomers of the fluorinated hydrofurans via a novel stereodivergent axial-to-central chirality transfer process.
- Yang, Shao-Qian,Wang, Yi-Fan,Zhao, Wei-Cheng,Lin, Guo-Qiang,He, Zhi-Tao
-
supporting information
p. 7285 - 7291
(2021/05/26)
-
- Gold catalyzed efficient preparation of dihydrobenzofuran from 1,3-enyne and phenol
-
A gold catalyzed formal intermolecular [2+3] cyclo-coupling of 1,3-enynes with phenols was developed to prepare dihydrobenzofuran derivatives with the addition of 2,6-dichloropyridine N-oxide, in which, a highly ortho-selective phenol SEAr functionalizati
- Wang, Yu-Jiang,Zhang, Yuan,Qiang, Zou,Liang, Jia-Ying,Chen, Zili
-
supporting information
p. 12607 - 12610
(2021/12/07)
-
- Fe-Catalyzed Selective Cyclopropanation of Enynes under Photochemical or Thermal Conditions
-
The nucleophilic Fe-complex Bu4N[Fe(CO)3(NO)] (TBA[Fe]) catalyzes the cyclopropanation of enynes to substituted propargyl cyclopropanes using diazoesters as carbene surrogates. The catalyst can be activated either thermally in the presence of catalytic amounts of 4-nitroanisole or under photochemical conditions. Cyclopropanation occurs selectively at the enyne moiety; alternative olefinic moieties remain intact.
- Picher, Marie-Idrissa,Plietker, Bernd
-
p. 340 - 344
(2020/01/11)
-
- Direct access to pentenedinitriles: Via Ni-catalyzed dihydrocyanation of 1,3-enynes
-
A highly regio-and stereoselective dihydrocyanation of 1,3-enynes was implemented by nickel/diphosphine catalysts. This reaction represents the first example of Ni-catalyzed dihydrocyanation of 1,3-enynes using TMSCN and MeOH as HCN surrogates. In this tr
- Fang, Xianjie,Gao, Jihui,Sun, Feilong
-
supporting information
p. 6858 - 6861
(2020/07/04)
-
- Triple-Bond Insertion Triggers Highly Regioselective 1,4-Aminomethylamination of 1,3-Enynes with Aminals Enabled by Pd-Catalyzed C-N Bond Activation
-
A highly chemo- and regioselective 1,4-aminomethylamination of simple enynes with aminals to allenic 1,5-diamines by taking advantage of C-N bond activation has been reported. The reaction proceeds under mild reaction conditions and can be performed under
- Zhang, Yanchen,Yu, Bangkui,Gao, Binjian,Zhang, Tianze,Huang, Hanmin
-
supporting information
(2019/01/21)
-
- Triple-Bond Insertion Triggers Highly Regioselective 1,4-Aminomethylamination of 1,3-Enynes with Aminals Enabled by Pd-Catalyzed C-N Bond Activation
-
A highly chemo- and regioselective 1,4-aminomethylamination of simple enynes with aminals to allenic 1,5-diamines by taking advantage of C-N bond activation has been reported. The reaction proceeds under mild reaction conditions and can be performed under
- Zhang, Yanchen,Yu, Bangkui,Gao, Binjian,Zhang, Tianze,Huang, Hanmin
-
supporting information
p. 535 - 539
(2019/01/24)
-
- Redox-Neutral Annulation of Alkynylcyclopropanes with N-Aryloxyamides via Rhodium(III)-Catalyzed Sequential C-H/C-C Activation
-
Alkynylcyclopropanes have been used for the first time as coupling partners in transition-metal-catalyzed C-H functionalization. Specifically, a Cp?RhIII-catalyzed regioselective annulation of alkynylcyclopropanes with N-aryloxyamides via redox
- Li, Yang,Shi, Dandan,He, Xin,Wang, Yongzhuang,Tang, Yuhai,Zhang, Junjie,Xu, Silong
-
p. 1588 - 1595
(2019/01/21)
-
- Rhodium(III)-Catalyzed Redox-Neutral C-H Activation/Annulation of N-Aryloxyacetamides with Alkynyloxiranes: Synthesis of Highly Functionalized 2,3-Dihydrobenzofurans
-
Alkynyloxiranes have been employed for the first time as effective coupling partners in Cp RhIII-catalyzed C-H functionalization reactions. Their annulation with N-aryloxyamides then offers a redox-neutral and efficient synthesis of functionali
- Li, Yang,Shi, Dandan,Tang, Yuhai,He, Xin,Xu, Silong
-
p. 9464 - 9470
(2018/07/05)
-
- Copper-catalyzed silylation reactions of propargyl epoxides: Easy access to 2,3-allenols and stereodefined alkenes
-
Efficient silylation reactions of propargyl epoxides catalyzed by copper catalysts have been developed. Under mild reaction conditions, tri- and tetra-substituted functionalized allenols and alkenes could be selectively obtained in moderate to high yields
- Chang, Xi-Hao,Liu, Zheng-Li,Luo, Yun-Cheng,Yang, Chao,Liu, Xiao-Wei,Da, Bing-Chao,Li, Jie-Jun,Ahmad, Tanveer,Loh, Teck-Peng,Xu, Yun-He
-
supporting information
p. 9344 - 9347
(2017/08/23)
-
- Pd-Catalyzed [3+2] cycloaddition of ketoimines with alkynes via directed sp3 C-H bond activation
-
The Pd(ii)-catalyzed oxidative [3+2] cycloaddition of N-(2-pyridyl) ketoimines with internal alkynes has been developed. The transformation is tolerant of extensive substitution on halogen, alkene, alkyne, hydroxyl, aryl and acyl groups, and allows facile assembly of multisubstituted pyrroles. This journal is the Partner Organisations 2014.
- Xie, Ying,Chen, Tengfei,Fu, Shaomin,Li, Xing-Shu,Deng, Yuanfu,Jiang, Huanfeng,Zeng, Wei
-
supporting information
p. 10699 - 10702
(2014/10/15)
-
- Iron-catalyzed preparation of trifluoromethyl substituted vinyl- and alkynylcyclopropanes
-
A convenient iron-catalyzed procedure to prepare trifluoromethylated vinyl- and alkynylcyclopropanes in a chemo- and diastereoselective manner is presented. The active diazo compound (trifluoromethyl diazomethane) is generated in situ and used in the conc
- Morandi, Bill,Cheang, Jeremy,Carreira, Erick M.
-
supporting information; experimental part
p. 3080 - 3081
(2011/08/04)
-
- Vinyl Cations. 41. Influence of 4-Aryl and 4-Alkyl Substituents on the ?-Route Solvolyses of Homopropargyl Esters
-
The four 4-substituted-homopropargyl tosylates and triflates 6b-e (R=phenyl, p-tolyl, anisyl, and cyclopropyl) have been synthesized and solvolyzed under various conditions, as have 2-cyclopropyl-1-cyclobutenyl triflate (11-OTf) and nonaflate (11-ONf).In addition, the solvolyses of pent-3-yn-1-yl tosylate (6a-OTs, R=methyl) and triflate (prepared previously) are reported.The ratios of C-3 ring to C-4 ring 3 ring/C4ring)> products are recorded for the reactions in various solvents.As expected, ring closure (kΔ) increases and solvent displacement (kS, SN2) decreases with decreasing nucleophilicity of solvent.Temperature effects are noted for the sovolyses of tosylates 6a-e in 100percent TFE buffered with Na2CO3 in which kΔ increases with increasing temperature.The result is explained by decomposition of the intimate ion pair with temperature, whereupon elimination to the enyne becomes smaller and ring closure (kΔ) increases at the expense of elimination.The possibility of intervention of nonclassical vinyl cations is discussed, as are other mechanistic implications.
- Collins, Clair J.,Hanack, Michael,Stutz, Herbert,Auchter, Gerhard,Schoberth, Winfried
-
p. 5260 - 5268
(2007/10/02)
-