Visible light-assisted chemistry of vinyl azides and its applications in organic synthesis

Abstract

Vinyl azides have emerged as highly versatile precursors in organic synthesis due to their rich reactivity driven by an excellent leaving-group ability of the molecular nitrogen. Over the years, significant...

Visible-Light-Triggered Synthesis of N-α-Ketoacylated Sulfoximines by Denitrogenative and Oxidative Functionalization of Vinyl Azides

“…Based on the earlier experimental results and existing literature reports, we have postulated a feasible mechanistic pathway, as illustrated in Scheme . In the initial step, hypervalent iodine­(III) reagent A emerges via a ligand exchange between NH-sulfoximine ( 2a ) and PIDA.…”

Multiple-cycle photochemical cascade reactions

“…58,59 In contrast to traditional thermolysis or UV irradiation, the visible light sensitization of vinyl azides in the presence of a PC provides a cleaner and more efficient method for generating 2 H -azirines through an EnT process under mild conditions. 60,61 Utilizing this innovative approach, the teams of Xiao and Lu have developed a photoredox catalytic cascade reaction that enables the in situ formation of 2 H -azirine 54-A followed by a formal (3 + 2) cyclization with alkyne 55 (Scheme 15a). 62 With 9-mesityl-10-methylacridinium perchlorate PC-57 as the organic PC, this protocol offers an efficient route to highly substituted pyrrole 56 in 92% yield.…”

Mechanochemical-assisted decarboxylative sulfonylation of α,β-unsaturated carboxylic acids with sodium sulfinate salts

“…It offers a new opportunity for synthesizing organic compounds with solvent-free organic mechanochemical reactions and unlocks new routes towards numerous compounds that are not attainable by other conventional methods. 9 In continuation of our interest in sustainable, green, and novel synthetic methodologies, 10 we hereby report an unprecedented mechanochemical-assisted decarboxylative sulfonylation of α,β-unsaturated carboxylic acids with sodium sulfinates using only potassium iodide as an activator with water ( η = 0.32 μL mg −1 ) as the liquid-assisted grinding additive (LAG) 11 at ambient temperature under ball milling in 10 min. The method works equally well on alkyl and aryl sulfinates at room temperature without needing any metal catalyst, oxidant, base, or inert environment.…”