羧化
化学
试剂
分子内力
胺气处理
小学(天文学)
组合化学
功能群
氨基甲酸酯
分子
基质(水族馆)
有机合成
羰基化
羧酸
立体化学
化学合成
三键
有机化学
分子间力
氨基甲酸
反应条件
保护组
甲酰胺
酰胺
作者
Xinlong Hu,Li‐Li Liao,Jincheng Xu,Jing‐Wei Yang,Jishan Wu,Shuo Zhang,Sheng‐Chao Wang,Jun‐Ping Yue,Yi Jiang,Guangmei Cao,Lei Song,Jian‐Heng Ye,Da‐Gang Yu
出处
期刊:Angewandte Chemie
[Wiley]
日期:2025-09-25
卷期号:64 (46): e202515737-e202515737
被引量:6
标识
DOI:10.1002/anie.202515737
摘要
α-Amino acid motifs, serving as essential building blocks, are ubiquitous in natural products, bioactive molecules and drugs. Despite significant advances in the synthesis of α-amino acids (α-AAs) using CO2 as carboxyl source, the direct α-C(sp3)-H carboxylation of primary amines, which are important organic chemical feedstocks, remains an attractive yet formidable challenge. Herein, we report the first visible-light-driven direct α-C(sp3)-H carboxylation of primary benzylamines with CO2, wherein CO2 acts dually as a transient protecting group and as the carboxyl source. This strategy enables efficient synthesis of diverse α-AAs under mild reaction conditions with a broad substrate scope and good functional group compatibility. Mechanistic studies indicate that an intermolecular hydrogen atom transfer (HAT) between the external HAT reagent and the carbamate intermediate, in situ-generated from primary amine and CO2, is followed by reduction and carboxylation to furnish α-AAs. Moreover, a complementary protocol for carboxylation of α-C(sp3)─H bonds in amides through an intramolecular 1,2-HAT pathway is also developed, obviating the need for an external HAT reagent and further expanding the synthetic utility of this methodology. These advances represent a versatile and practical platform for the synthesis of α-AAs from amine precursors using CO2.
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