Photoinduced Hydroarylation and Cyclization of Alkenes with Luminescent Platinum(II) Complexes

• Published in: Angewandte Chemie International Edition Vol. 60; no. 3; pp. 1383 - 1389
• Main Authors: Cheng, Hanchao, Lam, Tsz‐Lung, Liu, Yungen, Tang, Zhou, Che, Chi‐Ming
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 18.01.2021; Wiley Subscription Services, Inc
• Edition: International ed. in English
• Subjects: Alkenes; Aromatic compounds; aryl halides; Bromides; Chemistry; Chemistry, Multidisciplinary; hydroarylation; intramolecular cyclization; Irradiation; photocatalysis; Physical Sciences; Platinum; Radiation; Science & Technology; CATALYSIS; CARBON; ALKYLATION; STRATEGY; ARYLATION; platinum; aryl halides; ELECTRON-TRANSFER; REDUCTION; intramolecular cyclization; CONSTRUCTION; hydroarylation; photocatalysis; ANTI-MARKOVNIKOV HYDROARYLATION; POLYPYRIDYL COMPLEX
• ISSN: 1433-7851; 1521-3773
• DOI: 10.1002/anie.202011841

Photoinduced hydroarylation of alkenes is an appealing synthetic strategy for arene functionalization. Herein, we demonstrated that aryl radicals generated from electron‐deficient aryl chlorides/bromides could be trapped by an array of terminal/internal aryl alkenes in the presence of [Pt(O^N^C^N)] under visible‐light (410 nm) irradiation, affording anti‐Markovnikov hydroarylated compounds in up to 95 % yield. Besides, a protocol for [Pt(O^N^C^N)]‐catalyzed intramolecular photocyclization of acrylanilides to give structurally diverse 3,4‐dihydroquinolinones has been developed. In the presence of luminescent [Pt(O^N^C^N)] complexes under visible light (410 nm) irradiation, aryl radicals derived from reductive aryl‐chloride/bromide bond cleavage were trapped by aryl alkenes and afforded a series of anti‐Markovnikov hydroarylated compounds. [Pt(O^N^C^N)]‐catalyzed intramolecular photocyclization of acrylanilides gives structurally diverse 3,4‐dihydroquinolinones.