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Science. 2011 Nov 25;334(6059):1114-7. doi: 10.1126/science.1213920.

Discovery of an α-amino C-H arylation reaction using the strategy of accelerated serendipity.

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  • 1Merck Center for Catalysis, Department of Chemistry, Princeton University, Princeton, NJ 08544, USA.

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.

PMID:
22116882
[PubMed - indexed for MEDLINE]
PMCID:
PMC3266580
Free PMC Article
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