Journal
ACS CATALYSIS
Volume 8, Issue 8, Pages 7439-7444Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.8b02029
Keywords
Heck reaction; palladium catalysis; alkylation; epoxides; alkyl radicals
Categories
Funding
- Singapore Ministry of Education Academic Research Fund (Tier 1) [MOE2015-T1-001-166, 2016-T1-002-093]
- Nanyang Technological University
Ask authors/readers for more resources
The palladium-catalyzed intermolecular Heck type reaction of both cyclic and acyclic epoxides is reported with tolerance of typical polar groups and acidic protons. Suitable alkenes include styrenes, conjugate dienes, and some electron-deficient olefins. In reactions of aliphatic terminal epoxides, ring opening occurs selectively at terminal positions, and stereocenters of epoxides are fully retained. Mechanistic studies provide evidence for in situ conversion of epoxides to beta-halohydrins, generation of alkyl radicals, and radical addition to alkenes as key steps. Cyclovoltammetric de,termination of reduction potentials suggests that during activation of alkyl iodides by palladium(0) complexes, inner-sphere halogen abstraction is more likely than outer-sphere single electron transfer.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available