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- Title
Stereoselective Synthesis of Trisubstituted Alkenes by Nickel‐Catalyzed Benzylation and Alkene Isomerization.
- Authors
Zhao, Yunlong; Liu, Chen‐Fei; Lin, Leroy Qi Hao; Chan, Albert S. C.; Koh, Ming Joo
- Abstract
Catalytic strategies that provide stereoselective access to highly substituted alkenes from abundant monosubstituted substrates are exceedingly sought‐after but rare. Here, we show that a N‐heterocyclic carbene‐NiI catalytic species mediates efficient union of electronically polarized terminal olefins with benzyl chlorides, in the presence of trimethylsilyl triflate and trimethylamine additives, to generate trisubstituted boron‐ and arene‐containing trans alkenes in excellent regio‐ and stereoselectivities. Control experiments provide evidence for a mechanism involving branched‐selective Heck‐type benzylation that overrides substrate control, followed by trans‐selective 1,3‐hydrogen shift. The method represents a significant addition to the toolbox of reactions for the concise synthesis of unsaturated biologically active compounds.
- Subjects
BIOACTIVE compounds; ISOMERIZATION; ALKENES; BENZYL chloride; ADDITION reactions; STEREOSELECTIVE reactions
- Publication
Angewandte Chemie, 2022, Vol 134, Issue 26, p1
- ISSN
0044-8249
- Publication type
Academic Journal
- DOI
10.1002/ange.202202674