title: TEMPO-Promoted Domino Heck-Suzuki Arylation: Diastereoselective Cis-Diarylation of Glycals and Pseudoglycals.
abstract: A palladium-catalyzed regio- and diastereoselective diarylation of glycals and pseudoglycals, which is a kind of Heck-Suzuki arylation, is described. A wide range of arylboronic acids reacted under these conditions smoothly. Selectivity was C1-C2(α,α) in the case of glycals but C2-C3(β,β) for pseudoglycals. Quantum chemical analysis has been carried out to establish the reaction mechanism, which may involve Pd(II)/Pd(O). TEMPO plays a key role in the formation of diaryl glycoside due to its radical nature.
authors.affiliation: †Academy of Scientific and Innovative Research, Indian Institute of Integrative Medicine (CSIR), Jammu 180001, India.
authors.forename: Anil Kumar
authors.initials: AK
authors.lastname: Kusunuru
authors.affiliation: ‡Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER), S. A. S. Nagar Punjab 160062, India.
authors.forename: Chaitanya K
authors.initials: CK
authors.lastname: Jaladanki
authors.affiliation: †Academy of Scientific and Innovative Research, Indian Institute of Integrative Medicine (CSIR), Jammu 180001, India.
authors.forename: Madhu Babu
authors.initials: MB
authors.lastname: Tatina
authors.affiliation: ‡Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER), S. A. S. Nagar Punjab 160062, India.
authors.forename: Prasad V
authors.initials: PV
authors.lastname: Bharatam
authors.affiliation: †Academy of Scientific and Innovative Research, Indian Institute of Integrative Medicine (CSIR), Jammu 180001, India.
authors.forename: Debaraj
authors.initials: D
authors.lastname: Mukherjee
mesh_terms: D002384:Catalysis; D003497:Cyclic N-Oxides / Q000737:chemistry*; D006027:Glycosides / Q000737:chemistry*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D003497:Cyclic N-Oxides; D006027:Glycosides; D010165:Palladium; C003959:TEMPO