Literature DB >> 27786484

Synthesis of Secondary and Tertiary Alkylboranes via Formal Hydroboration of Terminal and 1,1-Disubstituted Alkenes.

Hilary A Kerchner1, John Montgomery1.   

Abstract

Copper-catalyzed functionalization of terminal or 1,1-disubstituted alkenes with bis(pinacolato)diboron and methanol provides formal hydroboration products with exceptional regiocontrol favoring the branched isomer. Pairing this procedure with photocatalytic cross-couplings using iridium and nickel cocatalysis provides an effective, highly regioselective procedure for the hydroarylation of terminal alkenes.

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Year:  2016        PMID： 27786484      PMCID： PMC5189986          DOI： 10.1021/acs.orglett.6b03090

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


  58 in total

1.  Nickel-catalyzed Negishi cross-couplings of secondary nucleophiles with secondary propargylic electrophiles at room temperature.

Authors:  Sean W Smith; Gregory C Fu
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

2.  Diverse Asymmetric Hydrofunctionalization of Aliphatic Internal Alkenes through Catalytic Regioselective Hydroboration.

Authors:  Yumeng Xi; John F Hartwig
Journal:  J Am Chem Soc       Date:  2016-05-20       Impact factor: 15.419

3.  A general strategy for regiocontrol in nickel-catalyzed reductive couplings of aldehydes and alkynes.

Authors:  Hasnain A Malik; Grant J Sormunen; John Montgomery
Journal:  J Am Chem Soc       Date:  2010-05-12       Impact factor: 15.419

4.  Alkene isomerization-hydroboration promoted by phosphine-ligated cobalt catalysts.

Authors:  Margaret L Scheuermann; Elizabeth J Johnson; Paul J Chirik
Journal:  Org Lett       Date:  2015-05-26       Impact factor: 6.005

5.  Dramatic effect of Lewis acids on the rhodium-catalyzed hydroboration of olefins.

Authors:  Christopher J Lata; Cathleen M Crudden
Journal:  J Am Chem Soc       Date:  2010-01-13       Impact factor: 15.419

6.  Lithiated carbamates: chiral carbenoids for iterative homologation of boranes and boronic esters.

Authors:  Jake L Stymiest; Guillaume Dutheuil; Adeem Mahmood; Varinder K Aggarwal
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

7.  Enantioselective synthesis of quaternary carbon stereogenic centers through copper-catalyzed conjugate additions of aryl- and alkylaluminum reagents to acyclic trisubstituted enones.

Authors:  Jennifer A Dabrowski; Matthew T Villaume; Amir H Hoveyda
Journal:  Angew Chem Int Ed Engl       Date:  2013-06-18       Impact factor: 15.336

8.  Regiocontrol in catalytic reductive couplings through alterations of silane rate dependence.

Authors:  Evan P Jackson; John Montgomery
Journal:  J Am Chem Soc       Date:  2015-01-05       Impact factor: 15.419

9.  Development of Enantiospecific Coupling of Secondary and Tertiary Boronic Esters with Aromatic Compounds.

Authors:  Marcin Odachowski; Amadeu Bonet; Stephanie Essafi; Philip Conti-Ramsden; Jeremy N Harvey; Daniele Leonori; Varinder K Aggarwal
Journal:  J Am Chem Soc       Date:  2016-07-22       Impact factor: 15.419

10.  Ligand Design for Rh(III)-Catalyzed C-H Activation: An Unsymmetrical Cyclopentadienyl Enables a Regioselective Synthesis of Dihydroisoquinolones.

Authors:  Todd K Hyster; Derek M Dalton; Tomislav Rovis
Journal:  Chem Sci       Date:  2015-01-01       Impact factor: 9.825
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  7 in total

1.  Enabling the Cross-Coupling of Tertiary Organoboron Nucleophiles through Radical-Mediated Alkyl Transfer.

Authors:  David N Primer; Gary A Molander
Journal:  J Am Chem Soc       Date:  2017-07-18       Impact factor: 15.419

2.  Earth-Abundant Transition Metal Catalysts for Alkene Hydrosilylation and Hydroboration: Opportunities and Assessments.

Authors:  Jennifer V Obligacion; Paul J Chirik
Journal:  Nat Rev Chem       Date:  2018-04-27       Impact factor: 34.035

3.  NHC Ligands Tailored for Simultaneous Regio- and Enantiocontrol in Nickel-Catalyzed Reductive Couplings.

Authors:  Hengbin Wang; Gang Lu; Grant J Sormunen; Hasnain A Malik; Peng Liu; John Montgomery
Journal:  J Am Chem Soc       Date:  2017-07-03       Impact factor: 15.419

4.  Cu-Catalyzed Hydroboration of Benzylidenecyclopropanes: Reaction Optimization, (Hetero)Aryl Scope, and Origins of Pathway Selectivity.

Authors:  Jose M Medina; Taeho Kang; Tuğçe G Erbay; Huiling Shao; Gary M Gallego; Shouliang Yang; Michelle Tran-Dubé; Paul F Richardson; Joseph Derosa; Ryan T Helsel; Ryan L Patman; Fen Wang; Christopher P Ashcroft; John F Braganza; Indrawan McAlpine; Peng Liu; Keary M Engle
Journal:  ACS Catal       Date:  2019-10-29       Impact factor: 13.084

5.  Enantioselective Rhodium(III)-Catalyzed Markovnikov Hydroboration of Unactivated Terminal Alkenes.

Authors:  James R Smith; Beatrice S L Collins; Matthew J Hesse; Mark A Graham; Eddie L Myers; Varinder K Aggarwal
Journal:  J Am Chem Soc       Date:  2017-06-30       Impact factor: 15.419

Review 6.  Emergence and Applications of Base Metals (Fe, Co, and Ni) in Hydroboration and Hydrosilylation.

Authors:  Sem Raj Tamang; Michael Findlater
Journal:  Molecules       Date:  2019-09-03       Impact factor: 4.411

7.  Computational design of high-performance ligand for enantioselective Markovnikov hydroboration of aliphatic terminal alkenes.

Authors:  Hiroaki Iwamoto; Tsuneo Imamoto; Hajime Ito
Journal:  Nat Commun       Date:  2018-06-12       Impact factor: 14.919
  7 in total

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