TY - JOUR
T1 - Picolinate-Directed Arene meta-C-H Amination via FeCl3 Catalysis
AU - Anugu, Raghunath Reddy
AU - Munnuri, Sailu
AU - Falck, John R.
N1 - Funding Information:
Financial support was provided by the Robert A. Welch Foundation (I-0011), Dr. Ralph and Marian Falk Medical Research Trust Bank of America, N.A., Trustee, and the USPHS NIH (RO1 HL139793). Dr. Adeniyi Michael Adebesin is thanked for insightful advice and critical commentary.
Publisher Copyright:
Copyright © 2020 American Chemical Society.
PY - 2020/3/18
Y1 - 2020/3/18
N2 - Direct C-H functionalization of aromatic compounds is a powerful tool for organic synthesis; however, differentiation among the ubiquitous and often chemically similar C-H bonds remains a significant challenge. Conflation with coordinating or directing groups incorporated into the intended substrate has helped address these limitations, although access to remote sites remains limited. Herein, we report an operationally simple and sustainable direct meta-selective H2N amination of benzylic and related aromatic picolinates under conditions mild enough to modify polyfunctional and late-stage molecules.
AB - Direct C-H functionalization of aromatic compounds is a powerful tool for organic synthesis; however, differentiation among the ubiquitous and often chemically similar C-H bonds remains a significant challenge. Conflation with coordinating or directing groups incorporated into the intended substrate has helped address these limitations, although access to remote sites remains limited. Herein, we report an operationally simple and sustainable direct meta-selective H2N amination of benzylic and related aromatic picolinates under conditions mild enough to modify polyfunctional and late-stage molecules.
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U2 - 10.1021/jacs.9b13753
DO - 10.1021/jacs.9b13753
M3 - Article
C2 - 32090542
AN - SCOPUS:85082096298
SN - 0002-7863
VL - 142
SP - 5266
EP - 5271
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 11
ER -