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Transient and Recyclable Halogenation Coupling (TRHC) for Isoflavonoid Synthesis with Site‐Selective Arylation
Author(s) -
Wan JiePing,
Tu Zhi,
Wang Yuyun
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201901025
Subject(s) - halogenation , chemistry , halogen , catalysis , halogen bond , aryl , combinatorial chemistry , coupling reaction , organic chemistry , medicinal chemistry , alkyl
A transient and recyclable C−H iodination has been designed for the synthesis of isoflavonoids through the domino reactions of o ‐hydroxyphenyl enaminones and aryl boronic acids in the presence of catalytic KI and Pd catalyst. Instead of the conventional cross‐coupling strategy employing pre‐halogenated substrates, this method transforms raw C−H bond by means of a transient C−H halogenation to smoothly relay the subsequent C‐arylation. Consequently, such a method avoids the pre‐functionalization for C−halogen bond installation as well as the generation of stoichiometric halogen‐containing waste following the cross‐coupled product, disclosing an intriguing new coupling protocol to forge the C−C bond in the virgin area between classical C−X (X=halogen) bond cross coupling and the C−H activation.