TY - JOUR
T1 - Discovery of an α-amino C-H arylation reaction using the strategy of accelerated serendipity
AU - McNally, Andrew
AU - Prier, Christopher K.
AU - MacMillan, David W.C.
PY - 2011/11/25
Y1 - 2011/11/25
N2 - 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.
AB - 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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U2 - 10.1126/science.1213920
DO - 10.1126/science.1213920
M3 - Article
C2 - 22116882
AN - SCOPUS:82255173962
SN - 0036-8075
VL - 334
SP - 1114
EP - 1117
JO - Science
JF - Science
IS - 6059
ER -