Metal-Free Multiple Carbon-Carbon and Carbon-Hydrogen Bond Activations via Charge-Switching Mechanism in Unstrained Diindolylmethanes

被引：6

作者：

Challa, Chandrasekhar

Varughese, Sunil

Suresh, Cherumuttathu H. ^{[1
]}

Lankalapalli, Ravi S. ^{[1
]}

机构：

[1] NIIST, CSIR, Chem Sci & Technol Div, Thiruvananthapuram 695019, Kerala, India

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 16期

关键词：

HYPERVALENT IODINE OXIDATION; NATURAL-PRODUCTS; CLEAVAGE; REARRANGEMENT; COMPLEX;

D O I：

10.1021/acs.orglett.7b01843

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A transformation of the unstrained phenol substituted 3,3'-diindolylmethanes (DIPMs) to 2,3'-diindolylketones (DIKs) by double C-C single bond cleavage with associated rearrangements, triggered by phenyliodine(III) diacetate (PIDA), is reported. Density functional theory studies reveal a mechanism involving multiple charge-switching steps by synergistic involvement of the two indole units with overall low activation energy. The indole charge-switching mechanism in DIPMs was further extended toward synthesis of a natural product motif cyclohepta[b]indole from biaryl appended DIBM.

引用

收藏

页码：4219 / 4222

页数：4

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