Literature DB >> 22612642

Methyl 2,2-difluoro-2-(fluorosulfonyl)acetate, a difluorocarbene reagent with reactivity comparable to that of trimethylsilyl 2,2-difluoro-2-(fluorosulfonyl)acetate (TFDA).

Steffen Eusterwiemann1, Henry Martinez, William R Dolbier.   

Abstract

Under specific high concentration, high temperature conditions, methyl 2,2-difluoro-2-(fluorosulfonyl)acetate (MDFA) has been found to act as a very efficient source of difluorocarbene, exhibiting carbene reactivity characteristics comparable to those exhibited by trimethylsilyl 2,2-difluoro-2-(fluorosulfonyl)acetate (TFDA). For example, in reaction with highly unreactive n-butyl acrylate and using only 2 equiv of MDFA, a yield of 76% of difluorocyclopropane product was obtained after 2 days.

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Year:  2012        PMID： 22612642     DOI： 10.1021/jo300876z

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  4 in total

Review 1.  Decarboxylative fluorination strategies for accessing medicinally- relevant products.

Authors:  Yupu Qiao; Lingui Zhu; Brett R Ambler; Ryan A Altman
Journal:  Curr Top Med Chem       Date:  2014       Impact factor: 3.295

2.  Lead Optimization of a Pyrrole-Based Dihydroorotate Dehydrogenase Inhibitor Series for the Treatment of Malaria.

Authors:  Sreekanth Kokkonda; Xiaoyi Deng; Karen L White; Farah El Mazouni; John White; David M Shackleford; Kasiram Katneni; Francis C K Chiu; Helena Barker; Jenna McLaren; Elly Crighton; Gong Chen; Inigo Angulo-Barturen; Maria Belen Jimenez-Diaz; Santiago Ferrer; Leticia Huertas-Valentin; Maria Santos Martinez-Martinez; Maria Jose Lafuente-Monasterio; Rajesh Chittimalla; Shatrughan P Shahi; Sergio Wittlin; David Waterson; Jeremy N Burrows; Dave Matthews; Diana Tomchick; Pradipsinh K Rathod; Michael J Palmer; Susan A Charman; Margaret A Phillips
Journal:  J Med Chem       Date:  2020-04-16       Impact factor: 7.446

3.  EEDi-5285: An Exceptionally Potent, Efficacious, and Orally Active Small-Molecule Inhibitor of Embryonic Ectoderm Development.

Authors:  Rohan Kalyan Rej; Changwei Wang; Jianfeng Lu; Mi Wang; Elyse Petrunak; Kaitlin P Zawacki; Donna McEachern; Ester Fernandez-Salas; Chao-Yie Yang; Lu Wang; Ruiting Li; Krishnapriya Chinnaswamy; Bo Wen; Duxin Sun; Jeanne Stuckey; Yunlong Zhou; Jianyong Chen; Guozhi Tang; Shaomeng Wang
Journal:  J Med Chem       Date:  2020-06-24       Impact factor: 7.446

4.  A computational triage approach to the synthesis of novel difluorocyclopentenes and fluorinated cycloheptadienes using thermal rearrangements.

Authors:  David Orr; Jonathan M Percy; Zoë A Harrison
Journal:  Chem Sci       Date:  2016-06-16       Impact factor: 9.825
  4 in total

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