Palladium-catalyzed desulfinylative C-C allylation of Grignard reagents and enolates using allylsulfonyl chlorides and esters

TETRAHEDRON

卷:65

Review

Volla, Chandra M. Rao¹  Dubbaka, Srinivas Reddy²  Vogel, Pierre¹ 

[1] Ecole Polytech Fed Lausanne, LGSA, CH-1015 Lausanne, Switzerland

[2] ETH, Organ Chem Lab, CH-8093 Zurich, Switzerland

关键词: Allylic alkylation;    Allylic arylation;    Homogenous catalysis;    Regioselective allylation;    Palladium complexes;    Sulfonate esters;    Sulfonyl chlorides;    Grignard reagents;   

DOI  :  10.1016/j.tet.2008.11.007

来源: Elsevier

【 摘 要 】

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.

【 授权许可】

Free