Solution-phase photochemical transformation
of 2-aroylbenzofurans: addition–elimination
Ramesh C. Kamboj
Received: 30 October 2013 / Accepted: 15 January 2014 / Published online: 1 February 2014
Ó Springer Science+Business Media Dordrecht 2014
Abstract An efﬁcient conversion of 2-aroylbenzofurans into arylbenzofuryl-
methanols through photoreduction has been described. In these molecules, the photo
transformation occurred through the initial addition of solvent followed by elimi-
nation involving c-hydrogen abstraction. The photoproduct distribution markedly
depends upon the substituent present on the benzofuran moiety.
Keywords 2-Aroylbenzofurans Á Photoreduction Á c-Hydrogen abstraction Á
Synthetic organic photochemistry—chemistry of the electronic excited states of a
molecule—differs from ground state chemistry and affords a convenient approach
to complex structures that are difﬁcult to obtain by traditional synthetic methods.
The photochemistry of O-heterocycles is a less developed area as compared to
carbon aromatics [1–4], such as benzene, naphthalene, and anthracene derivatives.
Numerous types of conjugated O-heterocyclic compounds [5, 6] play important
roles in both natural and artiﬁcial systems due to their particular photochemical and
photophysical properties. From synthetic and mechanistic perspectives, benzofuran
derivatives [7, 8] showing very interesting photochemical and photophysical
properties are among the most extensively investigated organic compounds.
Benzofuran  and its derivatives are widely distributed in nature, particularly
among the plant monarchy. The benzofuran derivatives hold importance in
molecular biology such as in the treatment of osteoporosis [10, 11], as anesthetic
agents [12, 13], inhibitors of platelets aggregations , inhibitors of xanthine
P. Jindal Á G. Sharma Á R. Arora Á R. C. Kamboj (&)
Department of Chemistry, Kurukshetra University, Kurukshetra 136119, Haryana, India
Res Chem Intermed (2015) 41:4465–4476