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- Title
(NHC)NiH‐Catalyzed Regiodivergent Cross‐Hydroalkenylation of Vinyl Ethers with α‐Olefins: Syntheses of 1,2‐ and 1,3‐Disubstituted Allyl Ethers.
- Authors
Chen, Weihao; Li, Yang; Chen, Yang; Ho, Chun‐Yu
- Abstract
Abstract: Cross‐hydroalkenylation of a vinyl ether (<bold>1</bold>) with an α‐olefin (<bold>2</bold>) 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., <bold>1</bold> as acceptor and <bold>2</bold> as donor) was controlled mostly by electronic effects through the catalyst–substrate interaction. Sterically bulkier alkenes (<bold>2</bold>) 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 <bold>1</bold> with either a vinyl silane or boronic ester.
- Subjects
NICKEL compounds; ALKENYLATION; VINYL ethers; HETEROCYCLIC chemistry; ALKENES; ALLYL ethers
- Publication
Angewandte Chemie, 2018, Vol 130, Issue 10, p2707
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201712693