Palladium-catalyzed anti-michael reductive heck reaction of α,β-unsaturated esters
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...
Saved in:
| Main Authors: | , , , , , |
|---|---|
| Other Authors: | |
| Format: | Article |
| Language: | English |
| Published: |
2022
|
| Subjects: | |
| Online Access: | https://hdl.handle.net/10356/154741 |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| Institution: | Nanyang Technological University |
| Language: | English |
| Summary: | 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. |
|---|