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

Andrew McNally, Christopher K. Prier, David W.C. MacMillan

Research output: Contribution to journalArticle

509 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)1114-1117
Number of pages4
JournalScience
Volume334
Issue number6059
DOIs
StatePublished - Nov 25 2011

All Science Journal Classification (ASJC) codes

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