Pd(II)-Catalyzed, Picolinamide-Aided γ-(sp2)-C-H Functionalization of Racemic and Enantiopure α-Methylbenzylamine and Phenylglycinol Scaffolds

被引：20

作者：

Bisht, Narendra ^{[1
]}

Singh, Prabhakar ^{[1
]}

Babu, Srinivasarao Arulananda ^{[1
]}

机构：

[1] Indian Inst Sci Educ & Res IISER Mohali, Dept Chem Sci, Sect 81,Manauli PO, Mohali 140306, Punjab, India

来源：

SYNTHESIS-STUTTGART | 2022年 / 54卷 / 18期

关键词：

amino alcohols; bidentate directing groups; biaryls; C-H functionalization; cross-coupling; alpha-methylbenzylamine; palladium; stereoselective synthesis; C-H BONDS; PALLADIUM-CATALYZED ARYLATION; DIRECTING GROUP; C(SP(3))-H FUNCTIONALIZATION; ASSISTED FUNCTIONALIZATION; CHIRAL AUXILIARY; C-3; POSITION; AMINO-ACIDS; ARYL AMINES; ACTIVATION;

D O I：

10.1055/a-1830-3962

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In this paper, we report the Pd(II)-catalyzed, picolinamide DG-aided sp(2) gamma-C-H functionalization and expansion of the library of enantiopure alpha-methylbenzylamine and phenylglycinol scaffolds. We have shown the synthesis of a wide range of racemic and enantiopure ortho-C-H arylated, alkylated, brominated, and iodinated alpha-methylbenzylamine and phenylglycinol scaffolds. Various racemic and R and S (chiral) sp(2) gamma-C-H functionalized alpha-methylbenzylamine and phenylglycinol scaffolds were synthesized with good enantiopurities. Racemic and enantiopure alpha-methylbenzylamine and phenylglycinol derivatives are important building blocks in organic synthesis and medicinal chemistry. Accordingly, this work contributes to the expansion of the libraries of alpha-methylbenzylamine and phenylglycinol motifs and substrate scope development through the Pd(II)-catalyzed bidentate directing group picolinamide-aided site-selective C-H activation and functionalization method.

引用

页码：4059 / 4094

页数：36

共 132 条

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