Anionic Indole N-carbamoyl N --> C translocation. A directed remote metalation route to 2-Aryl- and 2-heteroarylindoles. synthesis of benz[a]carbazoles and Indeno[1,2-b]indoles.
A new LDA-induced anionic N-C carbamoyl migration of 2-arylindoles (7) is reported. Treatment of N-carbamoylindoles 10 and 13, readily available by direct and ipso-borodesilylative Suzuki-Miyaura cross-coupling routes from 8 and 12, respectively, provides a general route to functionalized 2-arylindoles 11 and 14, respectively (Tables 1 and 2). The reaction has been applied to the synthesis of benzo[ a]carbazoles 16 and indeno[1,2- b]indoles 18, and its intramolecularity has been established by a crossover experiment (Scheme 4).
Department of Chemistry, Queen's University, Kingston, ON K7L 3N6, Canada.
Zhongdong
Z
Zhao
Ashley
A
Jaworski
Isabel
I
Piel
Victor
V
Snieckus
D000838:Anions / Q000737:chemistry; D001554:Benzene / Q000737:chemistry*; D002219:Carbamates / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D008670:Metals / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure
D000838:Anions; D002219:Carbamates; D007211:Indoles; D008670:Metals; C030374:indole; D001554:Benzene