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Review | Regular issue | Vol 96, No. 6, 2018, pp.997-1035
Published online, 14th March, 2018
DOI: 10.3987/REV-18-880
■ Construction of Unique Heterocyclic Frameworks by Photochemical Reaction of 5- and 6-Membered Heteroaromatics

Noriyoshi Arai* and Takeshi Ohkuma*

*Division of Applied Chemistry, Faculty of Engineering, Hokkaido University, Kita 13 Nishi 8, Kita-ku, Sapporo, Hokkaido 060-8628, Japan

Abstract

Photochemical reaction is an attractive synthetic method since it enables peculiar transformations that are not achievable under thermochemical reaction conditions. Construction of heterocyclic frameworks is one of the largest research fields in synthetic organic chemistry, but the utilization of photochemical reactions for heterocyclic-framework construction is limited to such reactions as typical [2+2] cycloaddition reaction, dye-sensitized generation of singlet oxygen, and photochemical radical generation. In this review, we focus on novel methods for the construction of unique molecular frameworks by means of photochemical reactions of heteroaromatic cyclic compounds, including mainly 5-membered heteroaromatics, furans, thiophenes, thiazoles, and oxazoles, as well as several 6-membered compounds. In some cases, heteroaromatic compounds act as acceptors of other photochemically excited molecules, such as 3(n-π*) of carbonyl compounds, and in other cases the heteroaromatic compounds themselves are excited to generate reactive species that participate in the unique bond-forming reactions.