Literature DB >> 23425080

Nickel-catalyzed cross-couplings of benzylic pivalates with arylboroxines: stereospecific formation of diarylalkanes and triarylmethanes.

Qi Zhou1, Harathi D Srinivas, Srimoyee Dasgupta, Mary P Watson.   

Abstract

We have developed a stereospecific nickel-catalyzed cross-coupling of benzylic pivalates with arylboroxines. The success of this reaction relies on the use of Ni(cod)2 as the catalyst and NaOMe as a uniquely effective base. This reaction has broad scope with respect to the arylboroxine and benzylic pivalate, enabling the synthesis of a variety of diarylalkanes and triarylmethanes in good to excellent yields and ee's.

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Year:  2013        PMID： 23425080      PMCID： PMC4218864          DOI： 10.1021/ja312087x

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


  38 in total

1.  Remote desymmetrization at near-nanometer group separation catalyzed by a miniaturized enzyme mimic.

Authors:  Chad A Lewis; Anna Chiu; Michele Kubryk; Jaume Balsells; David Pollard; Craig K Esser; Jerry Murry; Robert A Reamer; Karl B Hansen; Scott J Miller
Journal:  J Am Chem Soc       Date:  2006-12-27       Impact factor: 15.419

2.  Enantioselective preparation of 1,1-diarylethanes: aldehydes as removable steering groups for asymmetric synthesis.

Authors:  Thomas C Fessard; Stephen P Andrews; Hajime Motoyoshi; Erick M Carreira
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

3.  Palladium-catalyzed C(sp3)-H arylation of diarylmethanes at room temperature: synthesis of triarylmethanes via deprotonative-cross-coupling processes.

Authors:  Jiadi Zhang; Ana Bellomo; Andrea D Creamer; Spencer D Dreher; Patrick J Walsh
Journal:  J Am Chem Soc       Date:  2012-08-07       Impact factor: 15.419

4.  Arylation of α-pivaloxyl ketones with arylboronic reagents via Ni-catalyzed sp3 C-O activation.

Authors:  Kun Huang; Gang Li; Wei-Ping Huang; Da-Gang Yu; Zhang-Jie Shi
Journal:  Chem Commun (Camb)       Date:  2011-05-27       Impact factor: 6.222

5.  Nickel(0)-catalyzed Heck cross-coupling via activation of aryl C-OPiv bonds.

Authors:  Andrew R Ehle; Qi Zhou; Mary P Watson
Journal:  Org Lett       Date:  2012-02-15       Impact factor: 6.005

6.  Suzuki-Miyaura cross-coupling reactions of benzyl halides with potassium aryltrifluoroborates.

Authors:  Gary A Molander; Maxwell D Elia
Journal:  J Org Chem       Date:  2006-11-24       Impact factor: 4.354

7.  Enantioselective syntheses of (+)-sertraline and (+)-indatraline using lithiation/borylation-protodeboronation methodology.

Authors:  Stefan Roesner; Javier Mansilla Casatejada; Tim G Elford; Ravindra P Sonawane; Varinder K Aggarwal
Journal:  Org Lett       Date:  2011-10-13       Impact factor: 6.005

8.  Enantioselective addition of boronates to o-quinone methides catalyzed by chiral biphenols.

Authors:  Yi Luan; Scott E Schaus
Journal:  J Am Chem Soc       Date:  2012-12-03       Impact factor: 15.419

9.  Cross-coupling reactions of aryl pivalates with boronic acids.

Authors:  Kyle W Quasdorf; Xia Tian; Neil K Garg
Journal:  J Am Chem Soc       Date:  2008-10-08       Impact factor: 15.419

10.  Traceless directing group for stereospecific nickel-catalyzed alkyl-alkyl cross-coupling reactions.

Authors:  Margaret A Greene; Ivelina M Yonova; Florence J Williams; Elizabeth R Jarvo
Journal:  Org Lett       Date:  2012-05-08       Impact factor: 6.005
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  50 in total

1.  A General, Simple Catalyst for Enantiospecific Cross Couplings of Benzylic Ammonium Triflates and Boronic Acids: No Phosphine Ligand Required.

Authors:  Danielle M Shacklady-McAtee; Kelsey M Roberts; Corey H Basch; Ye-Geun Song; Mary P Watson
Journal:  Tetrahedron       Date:  2014-07-08       Impact factor: 2.457

Review 2.  Enantioselective and Enantiospecific Transition-Metal-Catalyzed Cross-Coupling Reactions of Organometallic Reagents To Construct C-C Bonds.

Authors:  Alan H Cherney; Nathaniel T Kadunce; Sarah E Reisman
Journal:  Chem Rev       Date:  2015-08-13       Impact factor: 60.622

3.  Nickel-Catalyzed Asymmetric Reductive Cross-Coupling To Access 1,1-Diarylalkanes.

Authors:  Kelsey E Poremba; Nathaniel T Kadunce; Naoyuki Suzuki; Alan H Cherney; Sarah E Reisman
Journal:  J Am Chem Soc       Date:  2017-04-13       Impact factor: 15.419

4.  Enantiospecific sp(2)-sp(3) coupling of secondary and tertiary boronic esters.

Authors:  Amadeu Bonet; Marcin Odachowski; Daniele Leonori; Stephanie Essafi; Varinder K Aggarwal
Journal:  Nat Chem       Date:  2014-06-08       Impact factor: 24.427

5.  Activation of C-O and C-N Bonds Using Non-Precious-Metal Catalysis.

Authors:  Timothy B Boit; Ana S Bulger; Jacob E Dander; Neil K Garg
Journal:  ACS Catal       Date:  2020-09-10       Impact factor: 13.084

6.  Breaking Amides using Nickel Catalysis.

Authors:  Jacob E Dander; Neil K Garg
Journal:  ACS Catal       Date:  2017-01-06       Impact factor: 13.084

7.  Accessing Both Retention and Inversion Pathways in Stereospecific, Nickel-Catalyzed Miyaura Borylations of Allylic Pivalates.

Authors:  Qi Zhou; Harathi D Srinivas; Songnan Zhang; Mary P Watson
Journal:  J Am Chem Soc       Date:  2016-09-02       Impact factor: 15.419

8.  Pd(0)-catalyzed 1,1-diarylation of ethylene and allylic carbonates.

Authors:  Vaneet Saini; Longyan Liao; Qiaofeng Wang; Ranjan Jana; Matthew S Sigman
Journal:  Org Lett       Date:  2013-09-18       Impact factor: 6.005

9.  Asymmetric synthesis via stereospecific C-N and C-O bond activation of alkyl amine and alcohol derivatives.

Authors:  Sarah M Pound; Mary P Watson
Journal:  Chem Commun (Camb)       Date:  2018-10-30       Impact factor: 6.222

10.  Diarylmethanes through an Unprecedented Palladium-Catalyzed C-C Cross-Coupling of 1-(Aryl)methoxy-1 H-Benzotriazoles with Arylboronic Acids.

Authors:  Manish K Singh; Mahesh K Lakshman
Journal:  ChemCatChem       Date:  2015-11-04       Impact factor: 5.686
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