861113-45-3Relevant articles and documents
Photocatalyzed site-selective C(sp3)-H sulfonylation of toluene derivatives and cycloalkanes with inorganic sulfinates
Cao, Shi,Gong, Lei,Lin, Yu-Mei,Lu, Cheng,Sha, Liyuan,Zhang, Shaonan
, p. 564 - 570 (2022/02/05)
The development of practical methods for the direct and selective C(sp3)-H functionalization of hydrocarbons is an attractive topic in synthetic chemistry. Although the radical-mediated hydrogen atom transfer (HAT) process has shown considerable potential in such reactions, it still faces fundamental problems associated with reactivity and selectivity. Herein, we report a convenient and economic approach to site-selective C(sp3)-H sulfonylation via photo-induced HAT catalysis. Employing a conjugated polycyclic quinone as a direct HAT photocatalyst, commercially available inorganic sulfinates as the sulfonylation source, copper triflate as an inexpensive oxidant, a variety of toluene derivatives and cycloalkanes were converted into biologically and synthetically interesting sulfone products under mild conditions. The mechanistic studies reveal that the reaction sequence involves direct HAT-induced radical formation and a subsequent copper-mediated organometallic process for the C-S bond formation. This method offers an appealing opportunity to furnish high value-added products from abundant hydrocarbon starting materials and inexpensive reagents.
