Trifluoromethyl aryl sulfonates (TFMS): An applicable trifluoromethoxylation reagent

Meng, Lei; Miao, Hang; Wang, Xueyuan; Zhang, Wen; Zhu, Chengjian; Lu, Xiaqiang; Shen, Jian; Qin, Yanru; Zhang, Haoyang; Sha, Sijia; Zhu, Yongqiang

doi:10.1016/j.tetlet.2019.04.033

Cited by 18 publications

(11 citation statements)

References 29 publications

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“…In this study, they also identified that a thermally stable trifluoromethoxide salt [K( cis -dicyclohexano-18-c-6)] + CF 3 O – was responsible for the success of this transformation. Recently, Lei, Zhu, and co-workers reported a new class of trifluoromethoxylation reagent, trifluoromethyl aryl sulfonates (TFMS) 8-110 , and applied them in the trifluoromethoxylation-iodination of arynes, yielding products 8-111 (Scheme b) . In this study, they systematically screened the crown ether, fluoride salts, solvent effect, and “I” sources.…”

Section: Multicomponent Reactions (Mcrs)mentioning

confidence: 99%

“…Recently, Lei, Zhu, and co-workers reported a new class of trifluoromethoxylation reagent, trifluoromethyl aryl sulfonates (TFMS) 8-110, and applied them in the trifluoromethoxylation-iodination of arynes, yielding products 8-111 (Scheme 141b). 605 In this study, they systematically screened the crown ether, fluoride salts, solvent effect, and "I" sources. Sulfonium ylides could be generated from the reaction of certain S-containing molecules with o-silylaryl triflates, which would then participate in the subsequent transformations.…”

Section: Other Nucleophile-triggered Mcrsmentioning

confidence: 99%

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o-Silylaryl Triflates: A Journey of Kobayashi Aryne Precursors

2021

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Arynes are among the most active organic intermediates and have found numerous applications in expeditious preparation of substituted arenes. In the past 20 years, chemists have witnessed a resurgence in aryne chemistry, which is mainly attributed by the extensive utilization of Kobayashi's method, a fluoride-induced removal of the TMS group with concomitant departure of its ortho OTf group on o-silylaryl triflates. Nowadays, o-silylaryl triflates are the most frequently employed aryne precursors. This review provides an overview of the history of Kobayashi's method, its methodological achievements, and its applications in the synthesis of natural products, bioactive molecules, and polycyclic aromatic hydrocarbons.

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Section: Multicomponent Reactions (Mcrs)mentioning

confidence: 99%

Section: Other Nucleophile-triggered Mcrsmentioning

confidence: 99%

o-Silylaryl Triflates: A Journey of Kobayashi Aryne Precursors

2021

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“…In 2019, Lei, Zhu, and co-workers discovered trifluoromethyl arenesulfonates (TFMS) as trifluoromethoxylation reagents, and successfully demonstrated their synthetic potency in the vicinal trifluoromethoxylation-iodination reaction of arynes (Scheme 30). 52 Interestingly, optimization studies also revealed that the combination of KF and cis-DCy-18-crown-6 gave better results for o-iodoaryl trifluoromethyl ether products.…”

Section: Scheme 29 Tfbz-enabled Trifluoromethoxylation-halogenation O...mentioning

confidence: 99%

Recent Advances in Construction of C(sp2)–O Bonds via Aryne Participated Multicomponent Coupling Reactions

Peng

Tan

2022

Synthesis

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Aryne chemistry is a powerful synthetic technique that forge new bonds on aromatic rings. The recent resurgence of aryne based multicomponent coupling strategy has led to an influx of methodologies for the mild synthesis of arene derivatives. In particular, these innovative discoveries broaden and streamlines approaches toward phenol ether motifs, which are prevalent structural component across a broad range of chemistry related research field. Herein, this review aims to provide a comprehensive overview on recent progress in construction of C(sp2)-O bonds via aryne induced multicomponent reactions. Special attention has been focused on elucidating the reaction design and mechanistic pathway.

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“…In cases of unsymmetrical arynes the regioselectivity was definitely low. Simultaneous activation of TFMS 57 (Scheme 44) and ortho-(trimethylsilyl)aryl triflates 74 by potassium fluoride in the presence of crown ethers and iodination reagents led to the formation of o-iodoaryl trifluoromethyl ethers 3 in moderate to high yields [138]. Trifluoromethoxylation of aryne species in situ-generated from ortho-(trimethylsilyl)aryl triflates 74 with TFMS 57 allowed to form the intermediate aryl anion, which further trapped with iodination reagents to give o-trifluoromethoxylated iodoarenes 3 as useful synthetic building blocks for many applications.…”

Section: Trifluoromethyl Arylsulfonates (Tfms)mentioning

confidence: 99%