TY - JOUR
T1 - Ruthenium-Catalyzed C-H Benzoxylation of tert-Benzamides with Aromatic Acids by Weak Coordination
AU - More, Nagnath Yadav
AU - Padala, Kishor
AU - Jeganmohan, Masilamani
N1 - Funding Information:
We thank the Department of Science and Technology DST-SERB (EMR/2014/000978), India, for support of this research. N.Y.M. thanks the CSIR for a fellowship.
Publisher Copyright:
© 2017 American Chemical Society.
PY - 2017/12/1
Y1 - 2017/12/1
N2 - A highly regioselective C-H benzoxylation of tertiary benzamides with aromatic acids by weak O-amide coordination in the presence of [{RuCl2(p-cymene)}2], AgSbF6, and (NH4)2S2O8 in 1,2-dichloroethane at 100 °C for 24 h to afford ortho-benzoxylated tertiary benzamides is described. Selectively, ortho-benzoxylated cyclic benzamides were converted into ortho-benzoxylated benzaldehydes by using Cp2ZrHCl at room temperature. Subsequently, substituted salicylic acids were prepared by deprotection of the ester and amide groups of ortho-benzoxylated cyclic benzamides.
AB - A highly regioselective C-H benzoxylation of tertiary benzamides with aromatic acids by weak O-amide coordination in the presence of [{RuCl2(p-cymene)}2], AgSbF6, and (NH4)2S2O8 in 1,2-dichloroethane at 100 °C for 24 h to afford ortho-benzoxylated tertiary benzamides is described. Selectively, ortho-benzoxylated cyclic benzamides were converted into ortho-benzoxylated benzaldehydes by using Cp2ZrHCl at room temperature. Subsequently, substituted salicylic acids were prepared by deprotection of the ester and amide groups of ortho-benzoxylated cyclic benzamides.
UR - http://www.scopus.com/inward/record.url?scp=85036529639&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.7b02495
DO - 10.1021/acs.joc.7b02495
M3 - Article
C2 - 29087195
AN - SCOPUS:85036529639
VL - 82
SP - 12691
EP - 12700
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 23
ER -