Palladium-catalyzed N-(2-pyridyl)sulfonyl-directed C(sp3)-H γ-arylation of amino acid derivatives

被引:196
作者
Rodriguez, Nuria [1 ]
Romero-Revilla, Jose A. [1 ]
Angeles Fernandez-Ibanez, M. [1 ]
Carretero, Juan C. [1 ]
机构
[1] Univ Autonoma Madrid, Fac Ciencias, Dept Quim Organ, E-28049 Madrid, Spain
关键词
C-H BONDS; COUPLING REACTIONS; FUNCTIONALIZATION; ACTIVATION; CARBONYLATION; ALKYLATION; INDOLINES; AMINATION; SP(2); ALKENYLATION;
D O I
10.1039/c2sc21162a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The direct Pd-catalyzed gamma-arylation of amino acid esters bearing a removable N-(2-pyridyl)sulfonyl directing group is described. A variety of N-(2-pyridyl)sulfonamide amino acid derivatives, including alpha-quaternary amino acid and beta-amino acid substrates, react with iodoarenes in the presence of Pd(OAc)(2) to provide gamma-arylated products in synthetically useful yields. An unprecedented remote C(sp(3))-H arylation of dipeptides is presented, illustrating the compatibility of the method with the presence of the peptidic bond. The process occurs without racemization at the C alpha center and the auxiliary controlling group can be easily installed and removed in the amino acid backbone. A bimetallic Pd-II gamma-metalated complex has been isolated and characterized showing the key role exerted by the (2-pyridyl)sulfonyl unit.
引用
收藏
页码:175 / 179
页数:5
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