Photoinduced Reaction of Triarylphosphines with Alkenes Forming Fused Tricyclic Phosphonium Salts

• Main Authors: Yusuke Masuda (1486120), Masumi Uno (11576681), Masahiro Murakami (8477)
• Format: Dataset
• Language: unknown
• Published: 2021
• Subjects: Biochemistry; Cell Biology; Genetics; Molecular Biology; Biotechnology; Infectious Diseases; Plant Biology; Biological Sciences not elsewhere classified; Chemical Sciences not elsewhere classified; phosphatricyclo ­[ 4; highly endergonic process; mild reaction conditions; visible light; photoinduced reaction; phosphorus atom; phenyl ring; dearomatizing transannulation; carbonic acid; Carbonic acid
• Online Access: https://doi.org/10.1021/acs.orglett.1c03168.s002

Herein reported is a photoinduced reaction of triarylphosphines with alkenes in the presence of carbonic acid. A drastic structural change occurs to produce fused tricyclic phosphonium salts having a phosphatricyclo­[4.3.0.0 2.9 ]­nonene core structure. The reaction was marked by dearomatizing transannulation of the phenyl ring, 1,2-migration of the phosphorus atom, and incorporation of an alkene. The highly endergonic process is promoted by cooperation of visible light with a photocatalyst under mild reaction conditions.