Work

Manganese-Catalyzed Cycloalkene Ring Expansion Synthesis of Azaheterocycles

Year: 2024

Type: article

Abstract: Herein, a Mn catalytic protocol has been developed for the cycloalkene ring expansion synthesis of azaheterocycles, allowing broad-substrate-scope access to pyridine and isoquinoline derivatives. The initial monoaddition of an azidyl radical to alkene and further as-generated C-radical addition to O 2, followed by intramolecular rearrangement and aromatization, showcase a distinct Mn-catalyzed radical reactivity mode. The reaction features a short reaction time and a broad substrate scope, with applications demonstrated in complex structure elaboration and gram-scale vismodegib synthesis.

Source: Organic Letters

DOI: 10.1021/acs.orglett.4c03194

Authors: Zhixin Wang, Hanxiao Xu, Xuanzhen Han, Shuaixin Fan, Jin Zhu

Institution: Nanjing University

Language: English

Topic: Radical Photochemical Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: National Natural Science Foundation of China, Jiangsu Science and Technology Department

Awards: G117299061, G2814365926, G6916446599