Journal
TETRAHEDRON
Volume 65, Issue 2, Pages 504-511Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2008.11.007
Keywords
Allylic alkylation; Allylic arylation; Homogenous catalysis; Regioselective allylation; Palladium complexes; Sulfonate esters; Sulfonyl chlorides; Grignard reagents
Categories
Funding
- Swiss National Science Foundation (Bern)
- Roche Research Foundation (Basel)
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2-Methylprop-2-ene-, prop-2-ene-, 1-methylprop-2-ene-, and (E)-but-2-enesulfonyl chlorides have been used as electrophilic partners in desulfinylative palladium-catalyzed C-C coupling with Grignard reagents and sodium salts of dimethyl malonate and methyl acetoacetate. Neopentyl alk-2-ene sulfonates can also be used as electrophilic partners in desulfinylative allylic arylations and allylic alkylations. The regioselectivity of the allylic arylation and alkylation depends on the nature of the catalyst. With PdCl2(PhCN)(2), (E)-crotyl derivatives are formed in high regioselectivity using either 1-methylprop-2-ene- or (E)-but-2-enesulfonyl chloride. (C) 2008 Elsevier Ltd. All rights reserved.
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