Light-Induced Transformations of Donor-Donor Diazo Compounds Derived from N-Sulfonylhydrazones.

Abstract

The donor-donor carbene chemistry field is underdeveloped and often relies on harsh reaction conditions, utilizing either thermal or oxidative process with or without transition-metal catalysts. In this review, we discussed the synthesis and transformation of donor-donor diazo compounds from N-sulfonylhydrazones in the presence of light and base. The N-sulfonylhydrazones are easily accessible from the corresponding carbonyl compounds and sulfonyl hydrazides through condensation. The in situ generated N-sulfonyl anion in the presence of base would undergo the N-S bond cleavage with the aid of light to generate the donor-donor diazo compounds. The donor-donor diazo compounds showed various reactivity in the presence of light for the C-C and C-X bond formation, cyclopropanation reactions, and synthesis of nitrogen, oxygen-containing heterocyclic compounds, which all are discussed under metal-free conditions.