Abstract
A general intermolecular anti-Michael reductive Heck reaction of α,β-unsaturated esters with organobromides has been developed. Most topical classes of aryl, heteroaryl, and vinyl bromides were found to efficiently react with a variety of internal conjugated alkenes. This protocol set up a platform toward diverse α-arylated 1,6-dicarbonyl frameworks found in natural products and drugs, which are still highly challenging targets in traditional α-arylation protocols because of competitive selectivity of enolation. A removable directing group, gram-scale reaction, and modification of complex molecules have additionally demonstrated that the anti-Michael reductive Heck reaction is a powerful complementary strategy to the classical α-arylation approaches. Preliminary mechanistic studies are consistent with our proposed mechanistic design.
Original language | English |
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Pages (from-to) | 7262-7268 |
Number of pages | 7 |
Journal | ACS Catalysis |
Volume | 10 |
Issue number | 13 |
DOIs | |
State | Published - 2 Jul 2020 |
Keywords
- 1,6-dicarbonyl frameworks
- anti-Michael selectivity
- palladacycle
- reductive Heck reaction
- removable directing group
- α-arylation