Palladium-catalyzed weak-chelation-assisted C4-selective nitration of indoles has been accomplished employing -butyl nitrite in the presence of oxone under molecular oxygen at a moderate temperature. Aerobic conditions, C4-selectivity, substrate scope, conversion to valuable aminated indoles, and late-stage natural product modifications are the important practical features.
Download full-text PDF |
Source |
---|---|
http://dx.doi.org/10.1021/acs.orglett.3c03921 | DOI Listing |
Chem Commun (Camb)
June 2024
Department of Chemistry, Indian Institute of Technology Madras, Chennai 600036, India.
A palladium-catalyzed dual C-H functionalization of substituted aromatic ketones and ester with maleimides leading to tricyclic heterocyclic molecules with good to excellent yield is reported. In this protocol, weak chelation of the carbonyl groups has been successfully utilized for the selective activation of the -methyl C(sp)-H bond instead of the -C(sp)-H bond in the presence of an external bidentate ligand Ac-Ile-OH. The reaction proceeds through two-fold C-H activation to generate a five-membered cyclic ring.
View Article and Find Full Text PDFJ Org Chem
May 2024
Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati 781039, India.
Palladium-catalyzed weak chelation-assisted oxidative cross-dehydrogenative coupling of arenes has been accomplished. The use of medicinally important pyridones as the intrinsic directing group, regioselectivity, 2-fold C-H activation, and late-stage modification of bioactive compounds are the important practical features.
View Article and Find Full Text PDFOrg Lett
February 2024
Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati 781039, India.
Palladium-catalyzed weak-chelation-assisted C4-selective nitration of indoles has been accomplished employing -butyl nitrite in the presence of oxone under molecular oxygen at a moderate temperature. Aerobic conditions, C4-selectivity, substrate scope, conversion to valuable aminated indoles, and late-stage natural product modifications are the important practical features.
View Article and Find Full Text PDFOrg Lett
January 2022
Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati 781039, India.
Palladium-catalyzed weak chelation-assisted regioselective C4-arylation of indoles has been accomplished using a readily available arene at moderate temperature. The C4-arylation, weak chelating benzoyl (Bz) directing group, cross-dehydrogenative coupling (CDC), broad substrate scope, and late-stage diversifications are the important practical features.
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!