Nickel‐Catalyzed Electroreductive Syntheses of Triphenylenes Using ortho‐Dihalobenzene‐Derived Benzynes. Issue 19 (26th July 2022)

• Record Type: Journal Article
• Authors: Li, Zhao‐Ming; Shuai, Bin; Ma, Cong; Fang, Ping; Mei, Tian‐Sheng
• Is Part Of: Chinese journal of chemistry. Volume 40:Issue 19(2022)
• Page Start: 2335
• Page End: 2344
• Publication Date: 2022-07-26
• Subjects: Electrochemistry -- Ni catalysis -- Benzyne -- Cyclotrimerization -- Cross coupling; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/cjoc.202200245
• Languages: English
• ISSNs: 1001-604X

Abstract

Comprehensive Summary: Electrochemical nickel‐catalyzed syntheses of triphenylenes by a) reductive trimerization of ortho ‐dibromobenzenes or ortho ‐bromoarylsulfurofluoridates, or b) reductive cross‐coupling of ortho ‐dibromobenzenes to 2, 2'‐diiodobiphenyls, are described. The former provides a practical means for the construction of triphenylene derivatives in up to 87% isolated yield at room temperature. For 1, 2‐dihalo‐3‐methylbenzenes and related ortho‐ trisubstituted substrates, trimerizations proceed with high substrate‐controlled regioselectivity for the non‐ C 3h symmetric triphenylene isomer. Abstract :