Photocatalytic Oxidative C(sp3)-H/N-H Cross-Dehydrogenative Coupling of Tertiary Anilines with Amides/Imides: Synthesis of N-Mannich Bases

被引：1

作者：

Adelibieke, Qiaerbati ^{[1
]}

Yusan, Bulunuer ^{[1
]}

Wang, Xiong ^{[1
]}

Huang, Shuai ^{[1
]}

Wusiman, Abudureheman ^{[1
,2
]}

机构：

[1] Xinjiang Normal Univ, Sch Chem & Chem Engn, Urumqi 830054, Xinjiang, Peoples R China

[2] Xinjiang Key Lab Energy Storage & Photoelectrocata, Urumqi 830054, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2025年 / 90卷 / 18期

关键词：

COPPER-CATALYZED AMIDATION; BOND FORMATION; SCHIFF; ISATIN; N; N-DIMETHYLANILINES; FORMYLATION; DERIVATIVES; HYDRAZONES; AMINATION; MECHANISM;

D O I：

10.1021/acs.joc.4c03164

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A photocatalytic method for the synthesis of N-Mannich bases has been developed through the C(sp3)-H/N-H cross-dehydrogenative coupling of N,N-dimethylanilines with amides/imides. This process utilizes 2,4,6-triphenylpyrylium tetrafluoroborate (TPT) as the photocatalyst and is conducted at ambient temperature and atmospheric air. Various N,N-dimethylanilines and the aromatic, heteroaromatic and aliphatic (cyclic) amides, as well as imides were successfully employed, yielding moderate to good results. Preliminary mechanistic and isotope-labeling studies indicate that the reaction likely proceeds via a single electron transfer pathway and involves an alpha-aminoalkyl radical intermediate.

引用

页码：6123 / 6133

页数：11