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Title: Palladium-catalyzed anti-michael reductive heck reaction of α,β-unsaturated esters
Authors: Guo, Tao
Ding, Yalan
Zhou, Lili
Xu, Haiyan
Loh, Teck-Peng
Wu, Xiaojin
Keywords: Science::Chemistry
Issue Date: 2020
Source: Guo, T., Ding, Y., Zhou, L., Xu, H., Loh, T. & Wu, X. (2020). Palladium-catalyzed anti-michael reductive heck reaction of α,β-unsaturated esters. ACS Catalysis, 10(13), 7262-7268.
Journal: ACS Catalysis
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.
ISSN: 2155-5435
DOI: 10.1021/acscatal.0c02414
Rights: © 2020 American Chemical Society. All rights reserved.
Fulltext Permission: none
Fulltext Availability: No Fulltext
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