CC BY ND NC 4.0 · SynOpen 2017; 01(01): 0097-0102
DOI: 10.1055/s-0036-1588559
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Triarylmethyl Cation Catalysis: A Tunable Lewis Acid Organo­catalyst for the Synthesis of Bisindolylmethanes

Nicholas G. Boekell, Dana J. Cerone, Maria M. Boucher, Phong K. Quach, Wilfried B. Tentchou Nganyak, Christine G. Reavis, Ifeanyi I. Okoh, Jordan O. A. Reid, Hayley E. Berg, Briana A. Chang, Cheyenne S. Brindle*
Acknowledgment is made to the Donors of the American Chemical Society Petroleum Research Fund for partial support of this research. We are grateful to the National Science Foundation (CHE-0619275 and CHE-0963165) for renovation and instrumentation grants that supported this research.
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Publication History

Received: 29 June 2017

Accepted after revision: 07 August 2017

Publication Date:
22 August 2017 (online)

Abstract

Triarylmethyl cations serve as tunable organocatalysts for the synthesis of bisindolylmethanes. The catalyst structure can be modified to increase or decrease reactivity as needed to match the requirements of the substrate. High yields are achieved for a variety of substrates by using these green catalysts. Catalyst tuning allows for the use of less reactive electrophiles by increasing the reactivity of the catalyst. Acid-sensitive products can be isolated under these mild reaction conditions.

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