Dong J1, Krasnova L, Finn MG, Sharpless KB.
Angew Chem Int Ed Engl. 2014 Sep 1;53(36):9430-48. doi: 10.1002/anie.201309399. Epub 2014 Aug 11.Aryl sulfonyl chlorides (e.g. Ts-Cl) are beloved of organic chemists as the most commonly used S(VI) electrophiles, and the parent sulfuryl chloride, O2 S(VI) Cl2 , has also been relied on to create sulfates and sulfamides. However, the desired halide substitution event is often defeated by destruction of the sulfur electrophile because the S(VI) Cl bond is exceedingly sensitive to reductive collapse yielding S(IV) species and Cl(-) . Read More