Palladium-Catalyzed Synthesis of 2,3-Disubstituted Benzofurans: An Approach Towards the Synthesis of Deuterium Labeled Compounds.
Palladium-catalyzed oxidative annulations between phenols and alkenylcarboxylic acids produced a library of benzofuran compounds. Depending on the nature of the substitution of the phenol precursor, either 2,3-dialkylbenzofurans or 2-alkyl-3-methylene-2,3-dihydrobenzofurans can be synthesized with excellent regioselectivity. Reactions between conjugated 5-phenylpenta-2,4-dienoic acids and phenol gave 3-alkylidenedihydrobenzofuran alkaloid motifs while biologically active 7-arylbenzofuran derivatives were prepared by starting from 2-phenylphenols. More interestingly, selective incorporation of deuterium from D2O has been discovered, which offers an attractive one-step method to access deuterated compounds.
Department of Chemistry, Indian Institute of Technology Bombay Powai, Mumbai - 400076, India E-mail: dmaiti@chem.iitb.ac.in.
Soumitra
S
Agasti
Department of Chemistry, Indian Institute of Technology Bombay Powai, Mumbai - 400076, India E-mail: dmaiti@chem.iitb.ac.in.
Soham
S
Maity
Department of Organic Chemistry, Stockholm University SE-106 91 Stockholm, Sweden E-mail: kalman@organ.su.se.
Kalman J
KJ
Szabo
Department of Chemistry, Indian Institute of Technology Bombay Powai, Mumbai - 400076, India E-mail: dmaiti@chem.iitb.ac.in.
Debabrata
D
Maiti
C–H activation; benzofurans; deuterium; palladium; synthetic methods