Arylglycine-derivative synthesis via oxidative sp³C–H functionalization of α-amino esters

Abstract

SummaryAn efficient method for the synthesis of arylglycine derivatives is described. The oxidative coupling reactions of naphthols and phenols with α-amino esters proceeded smoothly in the presence of meta-chloroperoxybenzoic acid as an oxidant under ambient conditions, to produce arylglycine derivatives in satisfactory yields.

Alternative Strategies Enabling Cross-Dehydrogenative Coupling: Access to C—C Bonds

“…芳基酚具有良好的羟基给电子效 应, 被认为是一类有潜力的亲核偶联试剂. 2012 年, 包 明等 [71] 发现间氯过氧苯甲酸(mCPBA)可以直接氧化 均具有良好的耐受性, 偶联反应发生在酚羟基的邻位, 具有极高的区域选择性(Schemes 25b, 26), 此外, 大位 阻的 1,3,5-三甲氧基苯也可以与甘氨酸酯发生 CDC 反 应. 此后, 李瀛等 [73] 以有机染料 Rhodamine 6G (Rh 6G) [74] .…”

Copper (I) Catalyzed Sp3 C‐H Arylation of N‐Arylglycine Ester Derivatives under Aerobic Conditions

“…Arylation of glycine derivatives with commercially available aryl partners could generate diverse arylglycine derivatives that represent important building blocks for drug development and natural product synthesis. In this direction, Bao and co‐workers recently reported mCPBA promoted α‐indolylation and α‐napthylation of glycine derivatives. Further, copper catalyzed CDC reaction for the synthesis of indolylglycine derivatives have been reported by Huo etal .…”

Intermolecular Amidation of Quinoline N-Oxides with Arylsulfonamides under Metal-Free Conditions

“…In the course of our continuing research on the dehydrogenative reaction of amine N -oxide under metal-free conditions, the intermolecular amidation of quinoline N -oxides with sulfonamides has been found to proceed in the presence of PhI­(OAc) 2 and PPh 3 through 1,3-dipolar [3 + 3]-cycloaddition. A new type of 1,3-dipolar cycloaddition of quinoline N -oxides with sulfonamides should provide the following synthetic advantages: (1) overcome the extremely poor reactivity of sulfonamides as nucleophiles and (2) realize quinoline N -oxides as 1,3-dipoles to provide various N -(quinolin-2-yl)­sulfonamides by cycloaddition.…”