Literature DB >> 19449876

Investigation of the scope and regiochemistry of alkynylboronate cycloadditions with sydnones.

Duncan L Browne1, Jérôme F Vivat, Andrew Plant, Enrique Gomez-Bengoa, Joseph P A Harrity.   

Abstract

The cycloaddition of alkynylboronates and sydnones provides a convenient and highly regioselective method for the synthesis of a broad range of di-, tri-, and tetrasubstituted pyrazole boronic esters. The origins of an observed regiochemical divergence in the reactions of terminal alkynylboronates with their more substituted analogues have been studied by DFT methods.

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Year:  2009        PMID: 19449876     DOI: 10.1021/ja902460n

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  7 in total

1.  One Pot Spiropyrazoline Synthesis via Intramolecular Cyclization/Methylation.

Authors:  Sureshbabu Dadiboyena; Ashton T Hamme
Journal:  Tetrahedron Lett       Date:  2011-05-18       Impact factor: 2.415

2.  Synthesis of 2H-indazoles by the [3 + 2] dipolar cycloaddition of sydnones with arynes.

Authors:  Yuesi Fang; Chunrui Wu; Richard C Larock; Feng Shi
Journal:  J Org Chem       Date:  2011-10-12       Impact factor: 4.354

3.  Synthesis of Novel Pyrazoles via [2+3]-Dipolar Cycloaddition Using Alkyne Surrogates.

Authors:  Sureshbabu Dadiboyena; Edward J Valente; Ashton T Hamme
Journal:  Tetrahedron Lett       Date:  2010-03-03       Impact factor: 2.415

4.  Synthesis and Tautomerism of Spiro-Pyrazolines.

Authors:  Sureshbabu Dadiboyena; Edward J Valente; Ashton T Hamme
Journal:  Tetrahedron Lett       Date:  2014-04-02       Impact factor: 2.415

5.  Efficient synthesis of 1,3-diaryl-4-halo-1H-pyrazoles from 3-arylsydnones and 2-aryl-1,1-dihalo-1-alkenes.

Authors:  Yiwen Yang; Chunxiang Kuang; Hui Jin; Qing Yang; Zhongkui Zhang
Journal:  Beilstein J Org Chem       Date:  2011-12-12       Impact factor: 2.883

Review 6.  [3 + 2]-Cycloaddition reaction of sydnones with alkynes.

Authors:  Veronika Hladíková; Jiří Váňa; Jiří Hanusek
Journal:  Beilstein J Org Chem       Date:  2018-06-05       Impact factor: 2.883

7.  Acrylic boronate: a multifunctional C3 building block for catalytic synthesis of rare organoborons and chemoselective heterobifunctional ligations.

Authors:  Shengjia Lin; Lucia Wang; Abhishek Sharma
Journal:  Chem Sci       Date:  2021-04-26       Impact factor: 9.825

  7 in total

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