Literature DB >> 20392113

Copper-catalyzed diboration of ketones: facile synthesis of tertiary alpha-hydroxyboronate esters.

Melissa L McIntosh1, Cameron M Moore, Timothy B Clark.   

Abstract

The diboration of ketones with the (ICy)CuOt-Bu catalyst was developed to provide access to tertiary alpha-hydroxyboronate esters. The (ICy)CuOt-Bu catalyst was generated in situ with (ICy)CuCl and NaOt-Bu to afford a more efficient catalyst than the preformed (ICy)CuOt-Bu. These conditions result in the diboration of various ketones in toluene at 50 degrees C in 2-22 h. Treatment of the resulting products with silica gel affords the corresponding alpha-hydroxyboronate esters.

Entities:  

Year:  2010        PMID： 20392113     DOI： 10.1021/ol100468f

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


  11 in total

1.  Alcohol, Aldehyde, and Ketone Liberation and Intracellular Cargo Release through Peroxide-Mediated α-Boryl Ether Fragmentation.

Authors:  Ramsey D Hanna; Yuta Naro; Alexander Deiters; Paul E Floreancig
Journal:  J Am Chem Soc       Date:  2016-09-30       Impact factor: 15.419

2.  Direct Synthesis of Secondary Benzylic Alcohols Enabled by Photoredox/Ni Dual-Catalyzed Cross-Coupling.

Authors:  Rauful Alam; Gary A Molander
Journal:  J Org Chem       Date:  2017-11-27       Impact factor: 4.354

3.  Stereospecific cross-coupling of secondary organotrifluoroborates: potassium 1-(benzyloxy)alkyltrifluoroborates.

Authors:  Gary A Molander; Steven R Wisniewski
Journal:  J Am Chem Soc       Date:  2012-10-01       Impact factor: 15.419

4.  Scope and mechanism of the Pt-catalyzed enantioselective diboration of monosubstituted alkenes.

Authors:  John R Coombs; Fredrik Haeffner; Laura T Kliman; James P Morken
Journal:  J Am Chem Soc       Date:  2013-07-18       Impact factor: 15.419

5.  β-Silyloxy Allylboronate Esters through an Aldehyde Borylation/Homologation Sequence.

Authors:  Gillian F Meyer; Maggie A Nistler; Andrey V Samoshin; Brennan D McManus; Taylor A Thane; Carl J Ferber; Gregory W O'Neil; Timothy B Clark
Journal:  Tetrahedron Lett       Date:  2020-05-29       Impact factor: 2.415

6.  α-Hydroxy boron-enabled regioselective access to bifunctional halo-boryl alicyclic ethers and α-halo borons.

Authors:  Lucia Wang; Shengjia Lin; Yawei Zhu; Daniel Ferrante; Timaf Ishak; Yuki Baba; Abhishek Sharma
Journal:  Chem Commun (Camb)       Date:  2021-04-12       Impact factor: 6.222

7.  Facile formation of β-hydroxyboronate esters by a Cu-catalyzed diboration/Matteson homologation sequence.

Authors:  Cameron M Moore; Casey R Medina; Peter C Cannamela; Melissa L McIntosh; Carl J Ferber; Andrew J Roering; Timothy B Clark
Journal:  Org Lett       Date:  2014-11-20       Impact factor: 6.005

Review 8.  Recent advances in Cu-catalyzed C(sp3)-Si and C(sp3)-B bond formation.

Authors:  Balaram S Takale; Ruchita R Thakore; Elham Etemadi-Davan; Bruce H Lipshutz
Journal:  Beilstein J Org Chem       Date:  2020-04-15       Impact factor: 2.883

9.  Enantioselective Cu(I)-catalyzed borylative cyclization of enone-tethered cyclohexadienones and mechanistic insights.

Authors:  Sandip B Jadhav; Soumya Ranjan Dash; Sundaram Maurya; Jagadeesh Babu Nanubolu; Kumar Vanka; Rambabu Chegondi
Journal:  Nat Commun       Date:  2022-02-14       Impact factor: 17.694

10.  Stereoselective formation of trisubstituted vinyl boronate esters by the acid-mediated elimination of α-hydroxyboronate esters.

Authors:  Weiye Guan; Alicia K Michael; Melissa L McIntosh; Liza Koren-Selfridge; John P Scott; Timothy B Clark
Journal:  J Org Chem       Date:  2014-07-14       Impact factor: 4.354
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