Literature DB >> 28263411

A Mild and Regiospecific Synthesis of Pyrazoleboranes.

Andrew W Brown1, Júlia Comas-Barceló1, Joseph P A Harrity1.   

Abstract

Alkynylboranes show unprecedented reactivity in their [4+2] cycloaddition of sydnones offering access to fully substituted pyrazoles within a few hours at room temperature. This method delivers synthetically valuable pyrazoleboranes with complete control of regioselectivity, and these intermediates can be further elaborated through functionalization of the C-B bond.
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  alkynylborane; cycloaddition; pyrazole; regioselective; sydnone

Year:  2017        PMID: 28263411     DOI: 10.1002/chem.201701019

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  4 in total

1.  Influence of Endo- and Exocyclic Heteroatoms on Stabilities and 1,3-Dipolar Cycloaddition Reactivities of Mesoionic Azomethine Ylides and Imines.

Authors:  Pier Alexandre Champagne; K N Houk
Journal:  J Org Chem       Date:  2017-10-06       Impact factor: 4.354

Review 2.  [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

3.  A Mild and Regioselective Route to Fluoroalkyl Aromatic Compounds via Directed Cycloaddition Reactions.

Authors:  David L Cousins; Yee Hwee Lim; Joseph P A Harrity
Journal:  J Org Chem       Date:  2022-07-08       Impact factor: 4.198

4.  Arylethynyltrifluoroborate Dienophiles for on Demand Activation of IEDDA Reactions.

Authors:  Zbigniew Zawada; Zijian Guo; Bruno L Oliveira; Claudio D Navo; He Li; Pedro M S D Cal; Francisco Corzana; Gonzalo Jiménez-Osés; Gonçalo J L Bernardes
Journal:  Bioconjug Chem       Date:  2021-07-15       Impact factor: 4.774

  4 in total

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