Heterogeneous Photocatalytic Ring Expansion of Cyclic Ketones for the Construction of Medium-Sized Lactams

被引：5

作者：

Dang, Mengzhen ^{[1
]}

Jia, Ruizhi ^{[1
]}

Tan, Kai ^{[2
]}

Hao, Danyang ^{[3
]}

Yang, Wenjing ^{[1
]}

Zhou, Cong-Ying ^{[2
]}

Guo, Zhen ^{[1
]}

机构：

[1] Taiyuan Univ Technol, Coll Mat Sci & Engn, Key Lab Interface Sci & Engn Adv Mat, Minist Educ, Taiyuan 030024, Shanxi, Peoples R China

[2] Jinan Univ, Coll Chem & Mat Sci, Guangdong Prov Key Lab Funct Supramol Coordinat Ma, Guangzhou 510632, Peoples R China

[3] Westlake Univ, Coll Engn, Hangzhou 310012, Zhejiang, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 06期

基金：

中国国家自然科学基金;

关键词：

CLOSING METATHESIS; CARBONYLATION;

D O I：

10.1021/acs.joc.3c02899

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Construction of medium-sized ring compounds remains challenging in synthetic chemistry. Herein, we describe the synthesis of medium-sized lactams via a photoinduced ring expansion of benzo-fused cyclic ketones using graphitic carbon nitride (g-C3N4) as a photocatalyst. The ring expansion protocol provided an efficient access to 8-10-membered lactams in good yields and displayed good tolerance to a range of functional groups. The mechanism studies revealed that the photochemical reaction proceeds via an intermediary of a nitrogen radical, which is generated through an oxidative hydrogen atom transfer (HAT) process.

引用

页码：4031 / 4036

页数：6

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