Report

Discovery of an α-Amino C–H Arylation Reaction Using the Strategy of Accelerated Serendipity

Science  25 Nov 2011:
Vol. 334, Issue 6059, pp. 1114-1117
DOI: 10.1126/science.1213920

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Abstract

Serendipity has long been a welcome yet elusive phenomenon in the advancement of chemistry. We sought to exploit serendipity as a means of rapidly identifying unanticipated chemical transformations. By using a high-throughput, automated workflow and evaluating a large number of random reactions, we have discovered a photoredox-catalyzed C–H arylation reaction for the construction of benzylic amines, an important structural motif within pharmaceutical compounds that is not readily accessed via simple substrates. The mechanism directly couples tertiary amines with cyanoaromatics by using mild and operationally trivial conditions.

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