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...
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sg-ntu-dr.10356-1547412022-01-05T08:58:10Z Palladium-catalyzed anti-michael reductive heck reaction of α,β-unsaturated esters Guo, Tao Ding, Yalan Zhou, Lili Xu, Haiyan Loh, Teck-Peng Wu, Xiaojin School of Physical and Mathematical Sciences Science::Chemistry Reductive Heck Reaction Anti-Michael Selectivity 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. We gratefully acknowledge funding from the National Natural Science Foundation of China (21602104), Natural Science Foundation of Jiangsu Province, China (BK 20160986), the Starting Funding of Research (3983500176) from Nanjing Tech University. We thank Dr. Victor Gray and Dr. Sanyang Han (from Cavendish Laboratory, University of Cambridge) for proofreading. 2022-01-05T08:58:10Z 2022-01-05T08:58:10Z 2020 Journal Article 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. https://dx.doi.org/10.1021/acscatal.0c02414 2155-5435 https://hdl.handle.net/10356/154741 10.1021/acscatal.0c02414 2-s2.0-85088369510 13 10 7262 7268 en ACS Catalysis © 2020 American Chemical Society. All rights reserved. |
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Science::Chemistry Reductive Heck Reaction Anti-Michael Selectivity Guo, Tao Ding, Yalan Zhou, Lili Xu, Haiyan Loh, Teck-Peng Wu, Xiaojin Palladium-catalyzed anti-michael reductive heck reaction of α,β-unsaturated esters |
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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. |
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School of Physical and Mathematical Sciences |
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School of Physical and Mathematical Sciences Guo, Tao Ding, Yalan Zhou, Lili Xu, Haiyan Loh, Teck-Peng Wu, Xiaojin |
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Article |
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Guo, Tao Ding, Yalan Zhou, Lili Xu, Haiyan Loh, Teck-Peng Wu, Xiaojin |
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Guo, Tao |
title |
Palladium-catalyzed anti-michael reductive heck reaction of α,β-unsaturated esters |
title_short |
Palladium-catalyzed anti-michael reductive heck reaction of α,β-unsaturated esters |
title_full |
Palladium-catalyzed anti-michael reductive heck reaction of α,β-unsaturated esters |
title_fullStr |
Palladium-catalyzed anti-michael reductive heck reaction of α,β-unsaturated esters |
title_full_unstemmed |
Palladium-catalyzed anti-michael reductive heck reaction of α,β-unsaturated esters |
title_sort |
palladium-catalyzed anti-michael reductive heck reaction of α,β-unsaturated esters |
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2022 |
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https://hdl.handle.net/10356/154741 |
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1722355375606333440 |