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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