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金(I)催化的串联 C-H 和 C-C 活化(断裂)。

Gold(I)-catalyzed tandem C-H and C-C activation (cleavage).

机构信息

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032 China.

出版信息

Org Lett. 2010 Jan 1;12(1):116-9. doi: 10.1021/ol902593f.

Abstract

(Cyclopropylidenecyclohexyl)benzene derivatives, a kind of methylenecyclopropane (MCP) containing a cyclohexyl group, can undergo an interesting tandem intramolecular C-H and C-C bond activation through dehydrogenated rearrangement in the presence of AuPPh(3)Cl/AgOTf by transferring three hydrogen atoms from cyclohexane to cyclopropane, affording the corresponding biaryl derivatives in moderate to good yields. The reaction mechanism has also been carefully investigated by deuterium labeling experiments and DFT calculations.

摘要

(环丙叉基环己基)苯衍生物是一种含有环己基的亚甲基环丙烷(MCP),在 AuPPh(3)Cl/AgOTf 的存在下,通过将环己烷中的三个氢原子转移到环丙烷中,经过脱氢重排,可以发生有趣的串联分子内 C-H 和 C-C 键活化反应,从而以中等至良好的收率得到相应的联苯衍生物。通过氘标记实验和 DFT 计算,还仔细研究了反应机理。

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