TY - JOUR
T1 - Free Amino Group-Directed ?-C(sp3)-H Arylation of α-Amino Esters with Diaryliodonium Triflates by Palladium Catalysis
AU - Pramanick, Pranab K.
AU - Zhou, Zhibing
AU - Hou, Zhen Lin
AU - Yao, Bo
N1 - Publisher Copyright:
© 2019 American Chemical Society.
PY - 2019/5/3
Y1 - 2019/5/3
N2 - Free amino group-directed C(sp3)-H functionalization of aliphatic amines is a fundamental challenge in synthetic organic chemistry. Also, the NH2-directed C(sp3)-H functionalization of α-amino acids and their derivatives remains barely explored. With palladium as the catalyst and Ag2O as the additive, we developed the first NH2-directed ?-C(sp3)-H arylation of α-amino esters with diaryliodonium triflates for the construction of synthetically useful ?-aryl-α-amino esters, and the result of the KIE study suggested that the catalytic reaction involved an irreversible C-H cleavage as the rate-determining step.
AB - Free amino group-directed C(sp3)-H functionalization of aliphatic amines is a fundamental challenge in synthetic organic chemistry. Also, the NH2-directed C(sp3)-H functionalization of α-amino acids and their derivatives remains barely explored. With palladium as the catalyst and Ag2O as the additive, we developed the first NH2-directed ?-C(sp3)-H arylation of α-amino esters with diaryliodonium triflates for the construction of synthetically useful ?-aryl-α-amino esters, and the result of the KIE study suggested that the catalytic reaction involved an irreversible C-H cleavage as the rate-determining step.
UR - https://www.scopus.com/pages/publications/85065023604
U2 - 10.1021/acs.joc.9b00605
DO - 10.1021/acs.joc.9b00605
M3 - Article
C2 - 30957504
AN - SCOPUS:85065023604
SN - 0022-3263
VL - 84
SP - 5684
EP - 5694
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 9
ER -