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光氧化还原/钯/上坡三重催化促进的脂肪族羧酸与芳基乙烯的顺式选择性脱羧烯丙基化反应。

Cis-Selective Decarboxylative Alkenylation of Aliphatic Carboxylic Acids with Vinyl Arenes Enabled by Photoredox/Palladium/Uphill Triple Catalysis.

机构信息

Collaborative Innovation Center of Henan Grain Crops, National Key Laboratory of Wheat and Maize Crop Science, College of Plant Protection , Henan Agricultural University , Wenhua Road No. 95 , Zhengzhou 450002 , China.

Key Laboratory of Tropical Medicinal Plant Chemistry of Ministry of Education, Collaborative Innovation Center of Tropical Biological Resources , Hainan Normal University , Haikou , Hainan 571158 , China.

出版信息

Org Lett. 2018 May 4;20(9):2559-2563. doi: 10.1021/acs.orglett.8b00712. Epub 2018 Apr 17.

DOI:10.1021/acs.orglett.8b00712
PMID:29664648
Abstract

An iridium photoredox catalyst in combination with phenanthroline-supported palladium catalyst catalyzes decarboxylative alkenylation of tertiary and secondary aliphatic carboxylic acids with vinyl arenes to deliver β-alkylated styrenes with Z-selectivity. A broad scope of aliphatic carboxylic acids, including amino acids, exhibit as amenable substrates, and external oxidant is not required. The reaction proceeds by synergistic utilization of both energy-transfer and electron-transfer reactivity of iridium photoredox catalyst merging with palladium-catalyzed hydride elimination and insertion.

摘要

铱光氧化还原催化剂与菲咯啉负载钯催化剂结合,可催化三级和二级脂肪族羧酸与芳基乙烯的脱羧烯丙基化反应,以 Z 选择性得到β-烷基取代的苯乙烯。该反应具有广泛的脂肪族羧酸底物范围,包括氨基酸,并且不需要外部氧化剂。反应通过铱光氧化还原催化剂的能量转移和电子转移反应性与钯催化的氢化物消除和插入的协同利用来进行。

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