Literature DB >> 26632981

One-Pot Homologation of Boronic Acids: A Platform for Diversity-Oriented Synthesis.

Calum W Muir1, Julien C Vantourout1,2, Albert Isidro-Llobet2, Simon J F Macdonald2, Allan J B Watson1.   

Abstract

Formal homologation of sp(2)-hybridized boronic acids is achieved via cross-coupling of boronic acids with conjunctive haloaryl BMIDA components in the presence of a suitably balanced basic phase. The utility of this approach to provide a platform for diversity-oriented synthesis in discovery medicinal chemistry is demonstrated in the context of the synthesis of a series of analogues of a BET bromodomain inhibitor.

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Year:  2015        PMID： 26632981     DOI： 10.1021/acs.orglett.5b03030

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


  8 in total

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Authors:  Melanie Trobe; Martin D Burke
Journal:  Angew Chem Int Ed Engl       Date:  2018-03-07       Impact factor: 15.336

2.  Toward Generalization of Iterative Small Molecule Synthesis.

Authors:  Jonathan W Lehmann; Daniel J Blair; Martin D Burke
Journal:  Nat Rev Chem       Date:  2018-03-07       Impact factor: 34.035

3.  Peridinin Is an Exceptionally Potent and Membrane-Embedded Inhibitor of Bilayer Lipid Peroxidation.

Authors:  Hannah M S Haley; Adam G Hill; Alexander I Greenwood; Eric M Woerly; Chad M Rienstra; Martin D Burke
Journal:  J Am Chem Soc       Date:  2018-11-02       Impact factor: 15.419

4.  Chemoselective oxidation of aryl organoboron systems enabled by boronic acid-selective phase transfer.

Authors:  John J Molloy; Thomas A Clohessy; Craig Irving; Niall A Anderson; Guy C Lloyd-Jones; Allan J B Watson
Journal:  Chem Sci       Date:  2016-10-27       Impact factor: 9.825

5.  C(sp3)-C(sp2) cross-coupling of alkylsilicates with borylated aryl bromides - an iterative platform to alkylated aryl- and heteroaryl boronates.

Authors:  Brandon A Vara; Matthieu Jouffroy; Gary A Molander
Journal:  Chem Sci       Date:  2016-09-09       Impact factor: 9.825

Review 6.  Sequential and iterative Pd-catalyzed cross-coupling reactions in organic synthesis.

Authors:  Patrick Dobrounig; Melanie Trobe; Rolf Breinbauer
Journal:  Monatsh Chem       Date:  2016-12-09       Impact factor: 1.451

7.  A Convenient, Rapid, Conventional Heating Route to MIDA Boronates.

Authors:  Andrew McGown; Anthony K Edmonds; Daniel Guest; Verity L Holmes; Chris Dadswell; Ramón González-Méndez; Charles A I Goodall; Mark C Bagley; Barnaby W Greenland; John Spencer
Journal:  Molecules       Date:  2022-08-09       Impact factor: 4.927

8.  The dioxasilepanyl group as a versatile organometallic unit: studies on stability, reactivity, and utility.

Authors:  Hayate Saito; Jun Shimokawa; Hideki Yorimitsu
Journal:  Chem Sci       Date:  2021-06-08       Impact factor: 9.825
  8 in total

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