Regioselective Arylative Ring‐Closing Reaction of 2‐Alkynylphenyl Derivatives: Formation of Arylated Benzoxazin‐2‐ones, Benzoxazin‐2‐amines and 2, 3‐Disubstituted Indoles. Issue 36 (22nd November 2016)

• Record Type: Journal Article
• Authors: Minami, Hideki; Kanayama, Takuya; Tanaka, Reishi; Okamoto, Noriko; Sueda, Takuya; Yanada, Reiko
• Is Part Of: European journal of organic chemistry. Issue 36(2016)
• Page Start: 5990
• Page End: 6000
• Publication Date: 2016-11-22
• Subjects: Regioselectivity -- Arylation -- Cyclization -- Alkynes -- Nitrogen heterocycles -- Oxygen heterocycles; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201601162
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : Copper‐catalysed arylative ring‐closing reactions of 2‐alkynylphenylcarbamates and 2‐alkynylphenylureas with diaryliodonium salts gave C, N ‐double‐arylated benzoxazin‐2‐ones and C ‐arylated benzoxazin‐2‐amines, respectively, both bearing fully substituted exocyclic olefins. On the other hand, the palladium‐catalysed arylative ring‐closing reaction of 2‐alkynylphenylcarbamates gave C ‐arylated 2, 3‐disubstituted indoles. Abstract : Copper‐catalysed arylative ring‐closing reactions of 2‐alkynylphenylcarbamates and 2‐alkynylphenylureas with diaryliodonium salts gave C, N ‐double‐arylated benzoxazin‐2‐ones and C ‐arylated benzoxazin‐2‐amines, respectively, both bearing fully substituted exocyclic olefins. The palladium‐catalysed arylative ring‐closing reaction of 2‐alkynylphenylcarbamates gave C ‐arylated 2, 3‐disubstituted indoles.