(NHC)NiH-Catalyzed Regiodivergent Cross-Hydroalkenylation of Vinyl Ethers with -Olefins: Syntheses of 1,2-and 1,3-Disubstituted Allyl Ethers

Chen, Weihao; Li, Yang; Chen, Yang; Ho, Chun-Yu

2018-03

10.1002/anie.201712693

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION   影响因子和分区

1433-7851

1521-3773

Cross-hydroalkenylation of a vinyl ether (1) with an -olefin (2) was first achieved by a set of [NHC-Ni(allyl)]BArF (NHC=N-heterocyclic carbene) catalysts. Both 1,2- and 1,3-disubstituted allyl ethers were obtained, highly selectively, by using NHCs of different sizes. In contrast, the chemoselectivity (i.e., 1 as acceptor and 2 as donor) was controlled mostly by electronic effects through the catalyst-substrate interaction. Sterically bulkier alkenes (2) were used as preferred donors compared to smaller alkenes. This electronic effect also served as a basis for the first tail-to-head cross-hydroalkenylations of 1 with either a vinyl silane or boronic ester.

allylic compounds electronic effects ethers N-heterocyclic carbenes nickel

SCI ; EI ; IC ; CCR

英语

NI期刊

第一 ; 通讯

SZ basic research fund[JCYJ 201708173000222]

Chemistry

Chemistry, Multidisciplinary

WOS:000426252400027

WILEY-V C H VERLAG GMBH

20180704791674

Catalysts ; Nickel ; Olefins ; Substrates

Nickel:548.1 ; Chemical Agents and Basic Industrial Chemicals:803 ; Chemical Products Generally:804 ; Organic Compounds:804.1

CHEMISTRY

Web of Science

Southern Univ Sci & Technol SUSTech, Dept Chem, Shenzhen Key Lab Full Spectral Solar Elect Genera, Shenzhen, Guangdong, Peoples R China

Chen, Weihao,Li, Yang,Chen, Yang,et al. (NHC)NiH-Catalyzed Regiodivergent Cross-Hydroalkenylation of Vinyl Ethers with -Olefins: Syntheses of 1,2-and 1,3-Disubstituted Allyl Ethers[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2018,57(10):2677-2681.

Chen, Weihao,Li, Yang,Chen, Yang,&Ho, Chun-Yu.(2018).(NHC)NiH-Catalyzed Regiodivergent Cross-Hydroalkenylation of Vinyl Ethers with -Olefins: Syntheses of 1,2-and 1,3-Disubstituted Allyl Ethers.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,57(10),2677-2681.

Chen, Weihao,et al."(NHC)NiH-Catalyzed Regiodivergent Cross-Hydroalkenylation of Vinyl Ethers with -Olefins: Syntheses of 1,2-and 1,3-Disubstituted Allyl Ethers".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 57.10(2018):2677-2681.