Catalytic Cascade Access to Biaryl-2-Methyl Acetates from Pyruvate O-Arylmethyl Ketoximes via the Palladium-Catalyzed C(sp2)H Bond Arylation and C-O Bond Solvolysis

被引：8

作者：

Shao, Ling-Yan ^{[1
]}

Xing, Li-Hao ^{[1
]}

Guo, Ying ^{[1
]}

Yu, Kun-Kun ^{[1
]}

Wang, Wei ^{[1
,2
]}

Liu, Hong-Wei ^{[1
]}

Liao, Dao-Hua ^{[1
]}

Ji, Ya-Fei ^{[1
]}

机构：

[1] East China Univ Sci & Technol, Sch Pharm, 130 Meilong Rd, Shanghai 200237, Peoples R China

[2] Univ New Mexico, Dept Chem & Chem Biol, MSC03 2060, Albuquerque, NM 87131 USA

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2018年 / 360卷 / 15期

基金：

中国国家自然科学基金;

关键词：

arylation; biaryl-2-methyl acetates; C(sp(2))-H bond activation; pyruvate ketoximes; solvolysis; MASKED BENZYL ALCOHOLS; H BONDS; C(SP(3))-H BONDS; DIRECTING GROUP; INTRAMOLECULAR AMINATION; SITE SELECTIVITY; BETA-ARYLATION; METHYL OXIMES; BORONIC ACIDS; FUNCTIONALIZATION;

D O I：

10.1002/adsc.201800216

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A catalytic cascade has been developed for the synthesis of biaryl-2-methyl acetates via a palladium-catalyzed ortho-C(sp(2))-H bond arylation of pyruvate O-arylmethyl ketoximes with aryl iodides followed by a solvolysis, in which the pyruvic ketoxime ester as a new auxiliary is employed to direct the C(sp(2))-H bond activation. The straightforward treatment of O-arylmethyl hydroxylamines and ethyl pyruvate with aryl iodides also provides the target products in a one-pot fashion. Furthermore, the new palladacycle intermediate is unambiguously confirmed by single-crystal X-ray diffraction analysis. A plausible reaction pathway is proposed for the Pd-catalyzed arylation-acetolysis sequence.

引用

页码：2925 / 2937

页数：13

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