TY - JOUR
T1 - Cobalt-Catalyzed Benzylic Borylation
T2 - Enabling Polyborylation and Functionalization of Remote, Unactivated C(sp3)-H Bonds
AU - Palmer, W. Neil
AU - Obligacion, Jennifer V.
AU - Pappas, Iraklis
AU - Chirik, Paul J.
N1 - Funding Information:
W.N.P. acknowledges the National Science Foundation (CHE-1265988) for financial support. J.V.O. acknowledges the 2014-2015 Bristol-Myers Squibb Graduate Fellowship in Synthetic Organic Chemistry and the Paul Maeder ’75 Fund for Energy and the Environment through the Andlinger Center. We thank Allychem for a generous gift of B2Pin2.
Publisher Copyright:
© 2015 American Chemical Society.
PY - 2016/1/27
Y1 - 2016/1/27
N2 - Cobalt dialkyl and bis(carboxylate) complexes bearing α-diimine ligands have been synthesized and demonstrated as active for the C(sp3)-H borylation of a range of substituted alkyl arenes using B2Pin2 (Pin = pinacolate) as the boron source. At longer reaction times, rare examples of polyborylation were observed, and in the case of toluene, all three benzylic C-H positions were functionalized. Coupling benzylic C-H activation with alkyl isomerization enabled a base-metal-catalyzed method for the borylation of remote, unactivated C(sp3)-H bonds.
AB - Cobalt dialkyl and bis(carboxylate) complexes bearing α-diimine ligands have been synthesized and demonstrated as active for the C(sp3)-H borylation of a range of substituted alkyl arenes using B2Pin2 (Pin = pinacolate) as the boron source. At longer reaction times, rare examples of polyborylation were observed, and in the case of toluene, all three benzylic C-H positions were functionalized. Coupling benzylic C-H activation with alkyl isomerization enabled a base-metal-catalyzed method for the borylation of remote, unactivated C(sp3)-H bonds.
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U2 - 10.1021/jacs.5b12249
DO - 10.1021/jacs.5b12249
M3 - Article
C2 - 26714178
AN - SCOPUS:84956794725
SN - 0002-7863
VL - 138
SP - 766
EP - 769
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 3
ER -