A metal-free photocatalytic method achieves the selective radical cyclization of 1,5-enynes to construct naphthalene skeletons. This method utilizes an in situ-formed electron donor-acceptor (EDA) complex between sulfonyl chlorides and catalytic TBAI, delivering 4-cyano-1-sulfonyl naphthalenes through a 6-endo cyclization or a 5-exo-trig addition/3-exo-trig cyclization/ring expansion sequence. This one-pot transformation exhibits broad substrate scope and excellent functional group tolerance, efficiently forging both C-S and C-C bonds.
Li et al. (Tue,) studied this question.
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