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

By A. McNally, Christopher K. Prier, D. MacMillan. Science, 2011

789 citations recorded by the source corpus.

An unanticipated photocatalytic carbon-carbon bond-forming reaction emerged from screening many unusual reagent combinations. 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.

Subfields: Organic Chemistry

View Paper: https://www.semanticscholar.org/paper/70ae0d7fdad2fa8ff0f8de2b9cee31e6da5ac5cb

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Citations in the corpus

• Planned Luck: How Incubators Can Facilitate Serendipity for Nascent Entrepreneurs Through Fostering Network Embeddedness (2020, background): “…sciences has shown that we can increase the probability of unexpected encounters, for example, by increasing the amount of chemical interactions (McNally et al., 2011; Pirnot et al., 2013) or by introducing agent-based systems that support browsing the internet and access serendipitous…”