Palladium-catalyzed desulfinylative C-C allylation of Grignard reagents and enolates using allylsulfonyl chlorides and esters |
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| Authors: | Chandra M. Rao Volla Pierre Vogel |
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| Affiliation: | a Laboratory of Glycochemistry and Asymmetric Synthesis (LGSA), Swiss Institute of Technology in Lausanne (EPFL), Batochime, CH 1015 Lausanne, Switzerland
b Laboratory of Organic Chemistry, ETH Zürich, CH-8093 Zürich, Switzerland |
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| Abstract: | 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. |
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| Keywords: | Allylic alkylation Allylic arylation Homogenous catalysis Regioselective allylation Palladium complexes Sulfonate esters Sulfonyl chlorides Grignard reagents |
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