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Efficient Heterogeneous Gold(I)‐Catalyzed Direct C( sp 2 )–C( sp ) Bond Functionalization of Arylalkynes through a Nitrogenation Process to Amides
Author(s) -
Nie Quan,
Yi Feiyan,
Huang Bin,
Cai Mingzhong
Publication year - 2017
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.201700783
Subject(s) - chemistry , phosphine , catalysis , surface modification , trimethylsilyl , trimethylsilyl azide , azide , triphenylphosphine , heterogeneous catalysis , combinatorial chemistry , organic chemistry , medicinal chemistry
The first heterogeneous gold(I)‐catalyzed direct C( sp 2 )–C( sp ) bond functionalization of arylalkynes through a nitrogenation process to amides has been achieved by using an ordered mesoporous silica (MCM‐41)‐immobilized phosphine gold(I) complex [MCM‐41‐PPh 3 ‐AuCl] as catalyst and silver carbonate (Ag 2 CO 3 ) as cocatalyst with trimethylsilyl azide (TMSN 3 ) as a nitrogen source, yielding a variety of amides in moderate to excellent yields under mild conditions. This heterogeneous phosphine gold(I) complex shows the same turnover numbers as the homogeneous chloro(triphenylphosphine)gold(I) (Ph 3 PAuCl) and can easily be recovered by simple filtration of the reaction solution and recycled at least eight times without significant loss of activity, providing a novel, efficient, practical and economic method for the synthesis of amides from alkynes.