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A Simple Aliphatic Diamine Auxiliary for Palladium‐Catalyzed Arylation of Unactivated β ‐C( sp 3 )‐H Bonds
Author(s) -
Lou Jiang,
Wang Quannan,
He Yuan,
Yu Zhengkun
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201801022
Subject(s) - chemistry , palladium , catalysis , methanol , diamine , aryl , denticity , alkynylation , surface modification , medicinal chemistry , nitrogen atom , organic chemistry , combinatorial chemistry , group (periodic table) , crystal structure , alkyl
Palladium‐catalyzed β ‐C( sp 3 ) ‐ H arylation of aliphatic acid derivatives was achieved by means of 2‐dimethylaminoethylamine auxiliary as a directing group. The β ‐C( sp 3 )‐H arylation reactions with aryl and heteroaryl iodides efficiently afforded the corresponding arylated hydrocinnamic acid derivatives. Direct β ‐C( sp 3 )‐H alkynylation, and arene C−H arylation and alkynylation were also realized under the same or slightly modified conditions. The aliphatic diamine auxiliary in the products could be readily removed by methanol in the presence of BF 3 ⋅ OEt 2 . In comparison with the widely used bidentate nitrogen‐containing directing groups, 2‐dimethylaminoethylamine is a simple, cheap, readily available and removable, and atom‐economical directing group for C−H functionalization.