Synthesis and Photocatalytic Reactivity of Vinylsulfonium Ylides

Klose, Immo; Misale, Antonio; Maulide, Nuno

doi:10.1021/acs.joc.6b01073

Cited by 19 publications

(6 citation statements)

References 87 publications

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“…When treated with a gold(I) catalyst, these compounds were shown to efficiently undergo S-to-O vinyl transfers (Scheme 112). 357 The reaction resembles a Smiles rearrangement and was proposed to occur in two steps. An initial 5- exo - trig cyclization through the attack of the carbonyl oxygen atom onto the activated vinyl substituent, followed by elimination to generate the final product.…”

Section: Sulfur Ylidesmentioning

confidence: 99%

Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts

et al. 2019

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Organosulfur compounds have long played a vital role in organic chemistry and in the development of novel chemical structures and architectures. Prominent among these organosulfur compounds are those involving a sulfur(IV) center, which have been the subject of countless investigations over more than a hundred years. In addition to a long list of textbook sulfur-based reactions, there has been a sustained interest in the chemistry of organosulfur(IV) compounds in recent years. Of particular interest within organosulfur chemistry is the ease with which the synthetic chemist can effect a wide range of transformations through either bond formation or bond cleavage at sulfur. This review aims to cover the developments of the past decade in the chemistry of organic sulfur(IV) molecules and provide insight into both the wide range of reactions which critically rely on this versatile element and the diverse scaffolds that can thereby be synthesized.

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Section: Sulfur Ylidesmentioning

confidence: 99%

Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts

et al. 2019

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“…Although Aggarwal had previously built on the ability of vinylsulfonium salts to undergo nucleophilic additions generating versatile sulfonium ylides in situ [ 31 – 34 ], no investigations into vinyl-substituted sulfonium ylides had been reported. When treated with an appropriate π-acidic catalyst, these compounds were shown to efficiently undergo S -to- O vinyl transfers (Scheme 15 ) [ 35 ]. The reaction resembles a Smiles rearrangement and was proposed to occur via two main steps, namely, an initial attack of the carbonyl oxygen atom onto the activated vinyl substituent in a 5- exo -trig manner followed by elimination to generate the product.…”

Section: Non-carbene-based Transition Metal-mediated Reactions Of Sulmentioning

confidence: 99%

Sulfur-Based Ylides in Transition-Metal-Catalysed Processes

et al. 2018

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Traditionally employed in the synthesis of small ring systems and rearrangement chemistry, sulfur-based ylides occupy a unique position in the toolbox of the synthetic organic chemist. In recent years a number of pioneering researchers have looked to expand the application of these unorthodox reagents through the use of transition metal catalysis. The strength and flexibility of such a combination have been shown to be of key importance in developing powerful novel methodologies. This chapter summarises recent developments in transition metal-catalysed sulfonium/sulfoxonium ylide reactions, as well as providing a historical perspective. In overviewing the successes in this area, the authors hope to encourage others into this growing field.

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“…Although Aggarwal had previously built on the ability of vinylsulfonium salts to undergo nucleophilic additions generating versatile sulfonium ylides in situ [31][32][33][34], no investigations into vinyl-substituted sulfonium ylides had been reported. When treated with an appropriate π-acidic catalyst, these compounds were shown to efficiently undergo S-to-O vinyl transfers (Scheme 15) [35]. The reaction resembles a Smiles rearrangement and was proposed to occur via two main steps, namely, an initial attack of the carbonyl oxygen atom onto the activated vinyl substituent in a 5-exo-trig manner followed by elimination to generate the product.…”

Section: Transition Metals As π-Acid Catalystsmentioning

confidence: 99%