Oxidant controlled regioselective mono- and di-functionalization reactions of coumarins.
C-3 alkylation of coumarins has been accomplished using cycloalkanes or alkylbenzenes in the presence of di-tert-butylperoxide (DTBP) and Fe(III) catalyst. Under metal free conditions and just by switching the oxidant from DTBP to TBHP, an exclusive C-4 cycloalkylation-C-3 peroxidation reaction takes place. During C-3 alkylation, the C-C bond formation occurs at the expense of an existing C-C bond, while the C-4 alkylation is associated with the formation of new C-C and C-O bonds.
Department of Chemistry, Indian Institute of Technology Guwahati, 781 039, Assam, India. patel@iitg.ernet.in.
Arghya
A
Banerjee
Sourav Kumar
SK
Santra
Nilufa
N
Khatun
Wajid
W
Ali
Bhisma K
BK
Patel
D000478:Alkylation; D003374:Coumarins / Q000737:chemistry*; D015394:Molecular Structure; D016877:Oxidants / Q000737:chemistry*; D010545:Peroxides / Q000737:chemistry*; D013237:Stereoisomerism; D020122:tert-Butylhydroperoxide / Q000737:chemistry*
D003374:Coumarins; D016877:Oxidants; D010545:Peroxides; C111570:di-tert-butyl peroxide; D020122:tert-Butylhydroperoxide