Journal
ORGANIC LETTERS
Volume 10, Issue 13, Pages 2617-2620Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol800307g
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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).
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