Premium
Palladium‐Catalysed Direct Desulfitative Arylation of Pyrroles using Benzenesulfonyl Chlorides as Alternative Coupling Partners
Author(s) -
Jin Rongwei,
Yuan Kedong,
Chatelain Emmanuelle,
Soulé JeanFrançois,
Doucet Henri
Publication year - 2014
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.201400736
Subject(s) - chemistry , palladium , regioselectivity , pyrrole , phosphine , catalysis , cleavage (geology) , reactivity (psychology) , medicinal chemistry , derivative (finance) , organic chemistry , combinatorial chemistry , engineering , economics , medicine , alternative medicine , geotechnical engineering , pathology , fracture (geology) , financial economics
The reactivity of pyrrole derivatives for palladium‐catalysed desulfitative arylation has been investigated. 1‐Methyl‐, 1‐phenyl‐ and 1‐benzylpyrroles were successfully coupled with a variety of benzenesulfonyl chlorides using a phosphine‐free catalyst. Highly regioselective arylations at carbon C2 of pyrroles were observed in all cases. A wide variety of substituents on the benzenesulfonyl derivative was tolerated. It should be noted that even bromo‐ and iodo‐benzenesulfonyl chlorides were successfully coupled with pyrrole derivatives without cleavage of the CBr or CI bonds, allowing further transformations. Surprisingly, with indoles, mixtures of C2‐ and C3‐arylation products were obtained.