Adolf von Baeyer proposed the structure of indole more than a century ago which has revolutionized organic and medicinal chemistry. Since its characterization, the synthesis of naturally occurring indole derivatives remains a challenge that motivates further developments of indole functionalization in synthetic chemistry. Specifically, the ubiquity of indoles makes them key building blocks for pharmaceuticals, agrochemicals, and functional materials. C-H functionalization of indoles is one of the most common methods to substitute different functional groups in indoles. Herein we reported CCC-NHC pincer Ir(III) complex catalyzed asymmetric C−H insertion reaction of α-aryl-α-diazoacetates with N-protected indoles. In this reaction, 3 mol % of catalyst loading was used to synthesize a variety of optically active indole derivatives bearing chiral functional groups at the C3 position.

Synthesis of CCC-NHC pincer Ir(III) complex and its application in C-H functionalization of Indoles with alpha-aryl-alpha-diazoacetates

ACS Fall 2021

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