TY - JOUR
T1 - The Versatile Reaction Chemistry of an Alpha-Boryl Diazo Compound
AU - Liu, Yao
AU - Puig De La Bellacasa, Raimon
AU - Li, Bo
AU - Cuenca, Ana Belén
AU - Liu, Shih Yuan
N1 - Funding Information:
Research reported in this publication was supported by the National Institute of General Medical Sciences of the National Institutes of Health under Award Number R01GM136920 and by Boston College start-up funds. R.P. and A.B.C. thank the Universitat Ramon Llull and “la Caixa” Foundation (2017-URL-Internac-010 grant), the MICINN (PID2020-113661GB-I00) grant, and the AGAUR SGR-00294 grant for support.
Publisher Copyright:
© 2021 American Chemical Society.
PY - 2021/9/8
Y1 - 2021/9/8
N2 - The first α-boryl diazo compound that is capable of engaging in classic synthetic organic diazo reaction chemistry is described. The diazomethyl-1,2-azaborine 1, which is a BN isostere of phenyldiazomethane, is significantly more stable than phenyldiazomethane; its reaction chemistry ranges from C-H activation, O-H activation, [3+2] cycloaddition, and halogenation, to Ru-catalyzed carbonyl olefination. The demonstrated broad range of reactivity of diazomethyl-1,2-azaborine 1 makes it an exceptionally versatile synthetic building block for the 1,2-azaborine heterocyclic motif.
AB - The first α-boryl diazo compound that is capable of engaging in classic synthetic organic diazo reaction chemistry is described. The diazomethyl-1,2-azaborine 1, which is a BN isostere of phenyldiazomethane, is significantly more stable than phenyldiazomethane; its reaction chemistry ranges from C-H activation, O-H activation, [3+2] cycloaddition, and halogenation, to Ru-catalyzed carbonyl olefination. The demonstrated broad range of reactivity of diazomethyl-1,2-azaborine 1 makes it an exceptionally versatile synthetic building block for the 1,2-azaborine heterocyclic motif.
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U2 - 10.1021/jacs.1c06112
DO - 10.1021/jacs.1c06112
M3 - Article
C2 - 34431676
AN - SCOPUS:85114728700
SN - 0002-7863
VL - 143
SP - 14059
EP - 14064
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 35
ER -