Journal
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS
Volume 183, Issue 12, Pages 2943-2955Publisher
TAYLOR & FRANCIS LTD
DOI: 10.1080/10426500802040349
Keywords
Bimetallic catalysis; Cu(II); Sn(II); diorganoselenides; selenium transfer; selenous acid
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A selenium transfer reaction from selenous acid to benzyl and alkyl halides is initiated in the presence of stannous chloride and a catalytic amount of cupric chloride resulting in the formation of the corresponding diorganoselenides and/or diorganodiselenides as the major products as indicated by 1H, 13C, 77Se NMR, and MS. The reaction is characterized by a dual-metal effect at the selenium activation and transfer step. Thus, initial reaction of stannous chloride, cupric chloride, and selenous acid gives rise to -Cu2Se. Selenium transfer from the latter to the organic halide takes place with additional assistance of stannous chloride.
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