☆ 4.4 Article

Iodine-Mediated Domino Protocol for the Synthesis of Benzamides from Ethylarenes via sp3 C-H Functionalization

SYNLETT (2015)

期刊

SYNLETT

卷 26, 期 12, 页码 1677-1682

出版社

GEORG THIEME VERLAG KG

DOI: 10.1055/s-0034-1380210

关键词

sp(3) C-H functionalization; benzamides; iodine; ethylarenes; tert-butyl hydroperoxide (TBHP)

类别

Chemistry, Organic

资金

CSIR, New Delhi [01(2427)/10/EMR-II]
UGC-SAP, New Delhi
CSIR, New Delhi
DST [SB/FT/CS-147/2013]

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Protocol

Reagent

摘要

An efficient, metal-free domino protocol for the synthesis of benzamides has been developed from ethylarenes using aqueous ammonia. The reaction proceeds through the formation of triiodomethyl ketone intermediate in the presence of iodine as the promoter and TBHP as an oxidant followed by nucleophilic substitution with aqueous ammonia, forming an amide. This operationally simple, functional-group-tolerant tandem approach provides an easy access to the broad range of biologically important benzamides.

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