FeCl3•6H2O as a Mild Catalyst for Nucleophilic Substitution of Symmetrical Bis(indoyl)methanes

被引：24

作者：

Chantana, Chayamon ^{[1
,2
]}

Jaratjaroonphong, Jaray ^{[1
,2
,3
]}

机构：

[1] Burapha Univ, Fac Sci, Dept Chem, Chon Buri 20131, Thailand

[2] Burapha Univ, Fac Sci, Ctr Excellence Innovat Chem, Chon Buri 20131, Thailand

[3] Burapha Univ, Res Unit Synthet Cpds & Synthet Analogues Form Na, Chon Buri 20131, Thailand

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 86卷 / 03期

关键词：

FRIEDEL-CRAFTS REACTIONS; ENANTIOSELECTIVE SYNTHESIS; INDOLE ALKALOIDS; RAPID SYNTHESIS; BIS(INDOLYL)METHANES; EFFICIENT; METHODOLOGIES; DERIVATIVES; ALCOHOLS; EXCHANGE;

D O I：

10.1021/acs.joc.0c02466

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In this paper, unsymmetrical bis(indolyl)methane (BIM) and 3-alkylindole derivatives are smoothly synthesized from symmetrical BIMs with a variety of nucleophiles including heteroaromatic/aromatic compounds, allylsilane and alkynylsilane. FeCl3 center dot 6H(2)O is found to be a mild and highly effective catalyst for this nucleophilic substitution reaction in which N-methyl-2-phenylindole behaves as a good leaving group in the C-sp(3)-C-sp(2) bond cleavage reaction. The operational ease, nonexpensive and environmentally friendly catalyst, mild reaction conditions, broad functional group tolerance, and scalability of this reaction strategy are advantages of the present procedure.

引用

页码：2312 / 2327

页数：16

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