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Diaryl Sulfoxides from Aryl Benzyl Sulfoxides: A Single Palladium‐Catalyzed Triple Relay Process
Author(s) -
Jia Tiezheng,
Bellomo Ana,
Montel Sonia,
Zhang Mengnan,
EL Baina Kawtar,
Zheng Bing,
Walsh Patrick J.
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201307172
Subject(s) - aryl , palladium , chemistry , sulfoxide , catalysis , triple bond , combinatorial chemistry , bond cleavage , alkyl , organic chemistry , medicinal chemistry , double bond
A novel approach to produce diaryl sulfoxides from aryl benzyl sulfoxides is reported. Optimization of the reaction conditions was performed using high‐throughput experimentation techniques. The [Pd(dba) 2 ]/NiXantPhos catalyst system successfully promotes a triple relay process involving sulfoxide α‐arylation, CS bond cleavage, and CS bond formation. The byproduct benzophenone is formed by an additional palladium‐catalyzed process. It is noteworthy that palladium‐catalyzed benzylative CS bond cleavage of sulfoxides is unprecedented. A wide range of aryl benzyl sulfoxides, as well as alkyl benzyl sulfoxides with various (hetero)aryl bromides were employed in the triple relay process in good to excellent yields (85–99 %). Moreover, aryl methyl sulfoxides, dibenzyl sulfoxides, and dimethylsulfoxide could be utilized to generate diaryl sulfoxides involving multiple catalytic cycles by a single catalyst.