Synthesis of Difluoromethylthioesters from Aldehydes

Guo, Shi‐Huan; Zhang, Xinglong; Pan, Gao‐Fei; Zhu, Xue‐Qing; Gao, Ya‐Ru; Wang, Yongqiang

doi:10.1002/anie.201710731

Cited by 53 publications

(25 citation statements)

References 73 publications

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“…In the presence of radical-clock type reagent, the ring-closure product was isolated (81b). Based on these preliminary results and previous literature, 145,[183][184][185][186][187][188][189][190] we proposed a radical mechanism, in which the difluoromethylthiyl radical was generated from either the homolysis event of…”

Section: Photo-induced C Sp2 -H Difluoromethylthiolation: Synthesis Omentioning

confidence: 58%

Exploration of new reaction tools for late-stage functionalization of complex chemicals

et al. 2019

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Chemistry has always had as a target the conversion of molecules into valuable materials. Nevertheless, the aim of past synthesis has primarily focused on achieving a given transformation, regardless of the environmental impact of the synthetic route. Given the current global situation, the demand for sustainable alternatives has substantially increased. Our group focuses on developing selective chemical transformations that benefit from mild conditions, improved atom economy, and that can make use of renewable feedstocks as starting materials. This account summarizes our work over the past two decades specifically regarding the selective removal, conversion, and addition of functional groups that can, later on, be applied at a late stage for the modification of complex molecules.

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Section: Photo-induced C Sp2 -H Difluoromethylthiolation: Synthesis Omentioning

confidence: 58%

Exploration of new reaction tools for late-stage functionalization of complex chemicals

et al. 2019

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“…The Wang group also reported a radical difluoromethylthiolation of aldehydes with PhSO 2 SCF 2 H (R3) (Scheme 18). 39 Various aryl, heteroaryl, alkyl, and alkenyl aldehydes could all be converted into the expected products, demonstrating a wide substrate scope. They proposed that t-BuOOH could directly abstract a hydrogen atom from aldehydes to generate a carbonyl radical.…”

Section: Scheme 17 Difluoromethylthiolation Of Aldehydes With Phso 2 mentioning

confidence: 99%

Recent Advances in Difluoromethylthiolation

Xiao

Zheng

et al. 2019

Synthesis

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The difluoromethylthio group (HCF2S), which has been identified as a valuable functionality in drug and agrochemical discovery, has received increased attention recently. Two strategies, difluoromethylation and direct difluoromethylthiolation, have been well established for HCF2S incorporation. The former strategy suffers from the need to prepare sulfur-containing substrates. In contrast, direct difluoromethylthiolation is straightforward and step-economic. This short review covers the recent advances in direct difluoromethylthiolation, including electrophilic, radical, and transition-metal-catalyzed or -promoted reactions.1 Introduction2 Electrophilic Difluoromethylthiolation3 Radical Difluoromethylthiolation4 Transition-Metal-Catalyzed or -Promoted Difluoromethylthiolation5 Conclusions and Perspectives

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“…In 2018, Wang and co-workers communicated the first example of direct thioesterification of aldehydes with aromatic thiosulfonates [62]. They showed that treatment of various aromatic, heteroaromatic, aliphatic, and α,β-unsaturated aldehydes 47 with commercially available PhSO 2 SCF 2 H as an efficient source of medicinally important SCF 2 H group in the presence of 2 equiv.…”

Section: Fluoroalkylation Of Aldehydes With Arso 2 Sr F Reagentsmentioning

confidence: 99%

Methods for the direct synthesis of thioesters from aldehydes: a focus review

Jabarullah

Jermsittiparsert

Melnikov

et al. 2019

Journal of Sulfur Chemistry

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Direct C-H bond functionalization chemistry allows the pot-, atom-, and step-economical and original construction of carbon-carbon and carbon-heteroatom bonds starting from hydrocarbons (or hydrocarbon fragments) without requiring pre-functionalization of the starting materials. In this context, synthesis of biologically and synthetically important thioesters through direct thioesterification of aldehydes has recently attracted considerable attention from organic synthetic communities, because aldehydes are cheap and widely abundant chemical materials. This review highlights up-todate developments and accomplishments in this interesting research arena with special emphasis on the mechanistic aspects of the reactions.

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Synthesis of Difluoromethylthioesters from Aldehydes

Cited by 53 publications

References 73 publications

Exploration of new reaction tools for late-stage functionalization of complex chemicals

Exploration of new reaction tools for late-stage functionalization of complex chemicals

Recent Advances in Difluoromethylthiolation

Methods for the direct synthesis of thioesters from aldehydes: a focus review

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