Abstract:An efficient, catalyst-free strategy
to construct diarylmethyl
sulfones via 1,6-conjugate addition/aromatization/sulfonylation reaction
of
para
-quinone methides with sulfonyl hydrazides
under mild and environmentally benign conditions has been developed.
The established protocol provided a highly chemo- and regioselectivity
synthesis of a diverse array of novel diarylmethyl sulfones with excellent
yields, and the reaction could be scaled up.
“…One month later, Zhu's group deposited another monoclinic crystal structure of the same compound with P21/c space group with the Cambridge Crystallographic Data Center (CCDC no. : 1583037) [14]. There is only one molecule in the asymmetric unit of this monoclinic structure.…”
“…One month later, Zhu's group deposited another monoclinic crystal structure of the same compound with P21/c space group with the Cambridge Crystallographic Data Center (CCDC no. : 1583037) [14]. There is only one molecule in the asymmetric unit of this monoclinic structure.…”
“…[180] Generation of imine quinone ketals in situ from the corresponding p-methoxy N-substituted anilines by PIDA, followed by sulfonylation with sodium sulfinates, led to 4-methoxy-3-sulfonyl N-substituted anilines in 17-98% yields. [181] The reaction between p-quinone methides 337 and sulfonyl hydrazides 338 [182] or sodium sulfinates 339 [183] resulted in substituted 4-(sulfonylmethyl)phenols 340 in high yields (Scheme 147). Similar products were also prepared by three-component reaction of aldehydes, sodium sulfinates, and di-or trimethoxybenzenes in the presence of Amberlyst-15 in water.…”
Section: (Scheme 131bmentioning
confidence: 99%
“…The reaction between p ‐quinone methides 337 and sulfonyl hydrazides 338 [182] or sodium sulfinates 339 [183] resulted in substituted 4‐(sulfonylmethyl)phenols 340 in high yields (Scheme 147). Similar products were also prepared by three‐component reaction of aldehydes, sodium sulfinates, and di‐ or trimethoxybenzenes in the presence of Amberlyst‐15 in water [184] …”
Oxidative coupling methodology is widely applied for the formation of carbon-carbon and carbon-heteroatom bonds. This review focuses on methods for oxidative sulfonylation of multiple bonds involving sulfonyl hydrazides, sulfinic acids and their salts as sulfonylation reagents. Under oxidative conditions, they generate sulfonyl radicals, trapped by multiple carbon-carbon bonds resulting in a variety of SO 2-containing products: mainly, vinyl and alkynyl sulfones, hydroxy-, keto, and halo-substituted sulfones, sulfonylated derivatives of carbo-and heterocycles. This exhaustive review summarizes 321 references from 1996 to 2020 with the specialization of the studies of the last five years, and is divided into the chapters according to the classes of compounds being sulfonylated.
“…In the same year, the Liu and Zhu group used the same sulfonylation reagent and found a new method for the synthesis of diaryl methylsulfones via sulfonylation of para-quinone methides (Scheme 51) [73]. The reaction occurred smoothly in the cosolvent of ethanol and water at 50 • C without the use of any catalyst.…”
The construction of a C-S bond is a powerful strategy for the synthesis of sulfur containing compounds including sulfides, sulfoxides, and sulfones. Recent methodological developments have revealed lots of novel protocols for C-S bond formation, providing easy access to sulfur containing compounds. Unlike traditional Ullmann typed C-S coupling reaction, the recently developed reactions frequently use non-halide compounds, such as diazo compounds and simple arenes/alkanes instead of aryl halides as substrates. On the other hand, novel C-S coupling reaction pathways involving thiyl radicals have emerged as an important strategy to construct C-S bonds. In this review, we focus on the recent advances on the synthesis of sulfides, sulfoxides, and sulfones from non-halide substrates involving C-S bond construction.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.