Literature DB >> 21043522

Efficient synthesis of 2,2-diaryl-1,1-difluoroethenes via consecutive cross-coupling reactions of 2,2-difluoro-1-tributylstannylethenyl p-toluenesulfonate.

Seung Yeon Han1, In Howa Jeong.   

Abstract

2,2-Difluoro-1-tributylstannylethenyl p-toluenesulfonate (2) was reacted with aryl iodides in the presence of 10 mol % of Pd(PPh(3))(4) and 10 mol % of CuI in DMF at 80 °C for 10-20 h to give the cross-coupled products 3 in 35-97% yields. Further coupling reaction of 3 with arylstannanes in the presence of 5 mol % of Pd(PPh(3))(4) and 3 equiv of LiBr in DMF at 100 °C for 2-24 h afforded the desired products 5 in 25-78% yields.

Entities:  

Year:  2010        PMID: 21043522     DOI: 10.1021/ol1024037

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  3 in total

1.  Designer HF-based fluorination reagent: highly regioselective synthesis of fluoroalkenes and gem-difluoromethylene compounds from alkynes.

Authors:  Otome E Okoromoba; Junbin Han; Gerald B Hammond; Bo Xu
Journal:  J Am Chem Soc       Date:  2014-10-02       Impact factor: 15.419

2.  2,2-difluorovinyl benzoates for diverse synthesis of gem-difluoroenol ethers by Ni-catalyzed cross-coupling reactions.

Authors:  Chun-Ming Chan; Pui-Yiu Lee; Bingnan Du; Leong-Hung Cheung; Xin Xu; Zhenyang Lin; Wing-Yiu Yu
Journal:  Nat Commun       Date:  2021-01-18       Impact factor: 14.919

3.  Consecutive cross-coupling reactions of 2,2-difluoro-1-iodoethenyl tosylate with boronic acids: efficient synthesis of 1,1-diaryl-2,2-difluoroethenes.

Authors:  Ju Hee Kim; Su Jeong Choi; In Howa Jeong
Journal:  Beilstein J Org Chem       Date:  2013-11-14       Impact factor: 2.883

  3 in total

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