Nickel-Catalyzed β,γ-Dicarbofunctionalization of Alkenyl Carbonyl Compounds via Conjunctive Cross-Coupling
Nickel-Catalyzed β,γ-Dicarbofunctionalization of Alkenyl Carbonyl Compounds via Conjunctive Cross-Coupling
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DOI：
10.1021/jacs.7b06567
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发表时间：
2017-08-09
影响因子：
15
通讯作者：
Engle, Keary M.
中科院分区：
文献类型：
--
作者：
Derosa, Joseph;Tran, Van T.;Engle, Keary M.
报道了镍催化的非共轭链烯、芳基碘和烷基锌试剂之间的交叉偶联反应。利用8-氨基喹啉导向基团实现了出色的区域控制，该基团可以很容易地裂解以揭开网状贝塔、伽马-二官能化羧酸产品的面纱。在优化的条件下，末端和内部的烯烃底物都以中等到优异的产率提供了相应的烷基/芳基双官能化产物。这里开发的方法代表了涉及C(SP(3))-C(SP(3))还原消除步骤的非共轭烯烃的第一个三组分1，2-二碳官能化。
A nickel-catalyzed conjunctive cross-coupling between non-conjugated alkenes, aryl iodides, and alkylzinc reagents is reported. Excellent regiocontrol is achieved utilizing an 8-aminoquinoline directing group that can be readily cleaved to unmask net beta,gamma-dicarbofunctionalized carboxylic acid products. Under optimized conditions, both terminal and internal alkene substrates provided the corresponding alkyl/aryl difunctionalized products in moderate to excellent yields. The methodology developed herein represents the first three-component 1,2-dicarbofunctionalization of non-conjugated alkenes involving a C(sp(3))-C(sp(3)) reductive elimination step.