Sulfonyl Hydrazides in Organic Synthesis: A Review of Recent Studies

Abstract

Sulfonyl hydrazides are widely used as organic reagents. Advances in the past decade are summarized in the following categories by key intermediates: (1) [RO2S.]; (2) RO2SSR; (3) [ArS.]; (4) [RO2S−]; (5) RSO2‐[Metal] species; (6) Ar‐[Metal] species; (7) RSX; (8) RS‐DBU; (9) nucleophilic amino group; (10) sulfonyl hydrazides as diazene or sulfinic acid surrogate. Reactions with alkenes, alkynes, aldehydes, alcohols, thiophenol, Grignard reagents, among others, are discussed. We hope this review will promote future research in this area.

Carbon nano-onion-mediated dual targeting of P-selectin and P-glycoprotein to overcome cancer drug resistance

“…19a for static culture or 19 b for dynamic culture of aHUVECs, the FSCNO-DH nanoparticles after incubating with cell culture medium can still target the aHUVECs regardless of the culturing conditions. This is probably due to the strong interaction between the sulfonyl group (in fucoidan) and amino group (on ASCNO nanoparticles) by reducing the nucleophilicity and basicity of the amino group to form sulfonamide-like stable interaction 36 , 37 , which ensures the stability of fucoidan on the nanoparticle surface. In order to show the fucoidan density is important for the targeting effect, FSCNO nanoparticles with reduced/low fucoidan (F low SCNO nanoparticles) were prepared.…”

Copper‐Catalyzed Decarboxylative Reductive Sulfonylation of α‐Oxocarboxylic Acids with Aryl Sulfonyl Hydrazines

“…In path I , the copper intermediate B was firstly formed via interaction of CuCl with the α‐oxocarboxylic acid 1 , which subsequently underwent decarboxylation to release CO 2 and form the acylcopper complex C . Meanwhile, the oxidative decomposition of sulfonyl hydrazides 2 into sulfur‐centered anion takes place, along with the release of N 2 and H 2 O [7d,19] . The sulfur‐centered anion interact with the acylcopper complex C to afford the active sulfonyl copper species D .…”

“…Finally, intermediate E experienced a reductive elimination process to provide the desired product 3 and the CuCl. In path II , the decomposition of sulfonyl hydrazides 2 to intermediate Ar 1 SO 2 CuCl F assisted with CuCl may be the initial step of the reaction, along with the release of N 2 and H 2 O [7d,19] . Then, intermediate F reacted with α‐oxocarboxylic acids 1 to produce the sulfonyl copper species G , which went through a decarboxylation process to afford intermediate H .…”

Facile Synthesis of Sulfonyl Chlorides/Bromides from Sulfonyl Hydrazides

“…Sulfonyl hydrazides are attractive targets because of their wide applications in organic synthesis, particularly in total synthesis [ 36 ]. Because of the high activity of sulfonyl chloride, they could react with hydrazine hydrate to synthesize various sulfonyl hydrazides [ 36 ].…”