Premium
Sonogashira–Hagihara Coupling towards Diaryl Alkynes Catalyzed by FeCl 3 ⋅6 H 2 O/Cationic 2,2'‐Bipyridyl
Author(s) -
Hung TzuTing,
Huang ChunMin,
Tsai FuYu
Publication year - 2012
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201100358
Subject(s) - aryl , sonogashira coupling , catalysis , cationic polymerization , chemistry , alkyl , coupling reaction , medicinal chemistry , solvent , organic chemistry , palladium
Abstract Efficient and environmentally benign one‐pot Sonogashira–Hagihara coupling of aryl iodides with 4‐aryl‐2‐methylbut‐3‐yn‐2‐ols catalyzed by an FeCl 3 ⋅ 6 H 2 O/cationic 2,2'‐bipyridyl system in water under air in the presence of zinc powder reductant was performed. Various aryl iodides and 4‐aryl‐2‐methylbut‐3‐yn‐2‐ols were used as reactants, which afforded moderate to high yields of cross‐coupled products. Although alkyl‐substituted 2‐methylbut‐3‐yn‐2‐ol could not be coupled with aryl iodides, the use of alkyl terminal alkynes under similar conditions provided the corresponding products in moderate yields. This reaction protocol was also used to synthesize both symmetric and asymmetric 1,4‐diarylbuta‐1,3‐diynes. This one‐pot iron‐catalyzed Sonogashira–Hagihara coupling reaction progressed without the use of an organic solvent, a copper cocatalyst, or an inert atmosphere, rendering it an environmentally friendly method with potential for practical applications.