Literature DB >> 32893388

Design and Synthesis of TY-Phos and Application in Palladium-Catalyzed Enantioselective Fluoroarylation of gem-Difluoroalkenes.

Tao-Yan Lin1,2, Zhangjin Pan2, Youshao Tu3, Shuai Zhu2, Hai-Hong Wu2, Yu Liu3, Zhiming Li1, Junliang Zhang1.   

Abstract

The first example of highly enantioselective fluoroarylation of gem-difluoroalkenes with aryl halides is presented by using a new chiral sulfinamide phosphine (Sadphos) type ligand TY-Phos. N-Me-TY-Phos can be easily synthesized on a gram scale from readily available starting materials in three steps. Salient features of this work including readily available starting materials, good yields, high enantioselectivities as well as broad substrate scope make this approach very practical and attractive. Notably, the asymmetric synthesis of an analogue of a biologically active molecule is also reported.
© 2020 Wiley-VCH GmbH.

Entities:  

Keywords:  TY-Phos; fluoroarylation; gem-difluoroalkene; ligand design; palladium

Year:  2020        PMID: 32893388     DOI: 10.1002/anie.202008262

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  4 in total

1.  Cu(II)-Catalyzed Unsymmetrical Dioxidation of gem-Difluoroalkenes to Generate α,α-Difluorinated-α-phenoxyketones.

Authors:  Suvajit Koley; Kaylee T Cayton; Gisela A González-Montiel; M Ramu Yadav; Douglas L Orsi; Andrew J Intelli; Paul Ha-Yeon Cheong; Ryan A Altman
Journal:  J Org Chem       Date:  2022-08-01       Impact factor: 4.198

2.  Synthesis of bioactive fluoropyrrolidines via copper(i)-catalysed asymmetric 1,3-dipolar cycloaddition of azomethine ylides.

Authors:  Xiao Xu; Longzhu Bao; Lu Ran; Zhenyan Yang; Dingce Yan; Chun-Jiang Wang; Huailong Teng
Journal:  Chem Sci       Date:  2021-12-07       Impact factor: 9.825

3.  Transition-Metal-Free Synthesis of Polyfunctional Triarylmethanes and 1,1-Diarylalkanes by Sequential Cross-Coupling of Benzal Diacetates with Organozinc Reagents.

Authors:  Baosheng Wei; Qianyi Ren; Thomas Bein; Paul Knochel
Journal:  Angew Chem Int Ed Engl       Date:  2021-03-17       Impact factor: 15.336

4.  Simultaneous construction of axial and planar chirality by gold/TY-Phos-catalyzed asymmetric hydroarylation.

Authors:  Pei-Chao Zhang; Yin-Lin Li; Jiafeng He; Hai-Hong Wu; Zhiming Li; Junliang Zhang
Journal:  Nat Commun       Date:  2021-07-29       Impact factor: 14.919

  4 in total

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