Literature DB >> 26679212

Nickel-Catalyzed Borylation of Benzylic Ammonium Salts: Stereospecific Synthesis of Enantioenriched Benzylic Boronates.

Corey H Basch1, Kelsey M Cobb1, Mary P Watson1.   

Abstract

We have developed a stereospecific, nickel-catalyzed cross-coupling of secondary benzylic ammonium salts and diboronate esters to deliver highly enantioenriched benzylic boronates. This reaction utilizes amine-derived electrophiles, which are readily available in high enantiopurity, and simple, inexpensive nickel catalysts. This reaction has broad scope, enabling synthesis of a variety of secondary benzylic boronates in good yields and excellent ee's.

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Year:  2015        PMID： 26679212      PMCID： PMC4809423          DOI： 10.1021/acs.orglett.5b03455

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


  48 in total

1.  Axially chiral P-N ligands for the copper catalyzed beta-borylation of alpha,beta-unsaturated esters.

Authors:  William J Fleming; Helge Müller-Bunz; Vanesa Lillo; Elena Fernández; Patrick J Guiry
Journal:  Org Biomol Chem       Date:  2009-04-15       Impact factor: 3.876

2.  Ipso-Borylation of Aryl Ethers via Ni-Catalyzed C-OMe Cleavage.

Authors:  Cayetana Zarate; Rubén Manzano; Ruben Martin
Journal:  J Am Chem Soc       Date:  2015-05-22       Impact factor: 15.419

3.  Highly enantioselective synthesis of tertiary boronic esters and their stereospecific conversion to other functional groups and quaternary stereocentres.

Authors:  Helen K Scott; Varinder K Aggarwal
Journal:  Chemistry       Date:  2011-11-03       Impact factor: 5.236

4.  Stereoselective preparation of β-aryl-β-boronyl enoates and their copper-catalyzed enantioselective conjugate reduction.

Authors:  Jinyue Ding; Jack Chang Hung Lee; Dennis G Hall
Journal:  Org Lett       Date:  2012-08-15       Impact factor: 6.005

5.  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

6.  Pt-catalyzed enantioselective diboration of terminal alkenes with B2(pin)2.

Authors:  Laura T Kliman; Scott N Mlynarski; James P Morken
Journal:  J Am Chem Soc       Date:  2009-09-23       Impact factor: 15.419

7.  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

8.  Cycloaddition of chiral tert-butanesulfinimines with trimethylenemethane.

Authors:  George Procopiou; William Lewis; Gareth Harbottle; Robert A Stockman
Journal:  Org Lett       Date:  2013-04-04       Impact factor: 6.005

9.  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

Review 10.  Homologation and alkylation of boronic esters and boranes by 1,2-metallate rearrangement of boronate complexes.

Authors:  Stephen P Thomas; Rosalind M French; Vishal Jheengut; Varinder K Aggarwal
Journal:  Chem Rec       Date:  2009       Impact factor: 6.771
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  20 in total

1.  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

2.  Vinylation of Benzylic Amines via C-N Bond Functionalization of Benzylic Pyridinium Salts.

Authors:  Weiye Guan; Jennie Liao; Mary P Watson
Journal:  Synthesis (Stuttg)       Date:  2018-06-08       Impact factor: 3.157

3.  Harnessing Alkyl Amines as Electrophiles for Nickel-Catalyzed Cross Couplings via C-N Bond Activation.

Authors:  Corey H Basch; Jennie Liao; Jianyu Xu; Jacob J Piane; Mary P Watson
Journal:  J Am Chem Soc       Date:  2017-04-05       Impact factor: 15.419

4.  Deaminative Reductive Cross-Electrophile Couplings of Alkylpyridinium Salts and Aryl Bromides.

Authors:  Jennie Liao; Corey H Basch; Megan E Hoerrner; Michael R Talley; Brian P Boscoe; Joseph W Tucker; Michelle R Garnsey; Mary P Watson
Journal:  Org Lett       Date:  2019-03-27       Impact factor: 6.005

5.  Nickel-Catalyzed Enantioconvergent Borylation of Racemic Secondary Benzylic Electrophiles.

Authors:  Zhaobin Wang; Shoshana Bachman; Alexander S Dudnik; Gregory C Fu
Journal:  Angew Chem Int Ed Engl       Date:  2018-08-19       Impact factor: 15.336

6.  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

7.  Harnessing Alkylpyridinium Salts as Electrophiles in Deaminative Alkyl-Alkyl Cross-Couplings.

Authors:  Shane Plunkett; Corey H Basch; Samantha O Santana; Mary P Watson
Journal:  J Am Chem Soc       Date:  2019-01-30       Impact factor: 15.419

8.  Rhodium-catalyzed asymmetric hydroboration of γ,δ-unsaturated amide derivatives: δ-borylated amides.

Authors:  G L Hoang; S Zhang; J M Takacs
Journal:  Chem Commun (Camb)       Date:  2018-05-08       Impact factor: 6.222

9.  Transforming Benzylic Amines into Diarylmethanes: Cross-Couplings of Benzylic Pyridinium Salts via C-N Bond Activation.

Authors:  Jennie Liao; Weiye Guan; Brian P Boscoe; Joseph W Tucker; John W Tomlin; Michelle R Garnsey; Mary P Watson
Journal:  Org Lett       Date:  2018-05-10       Impact factor: 6.005

10.  Nickel-Catalyzed, Stereospecific C-C and C-B Cross-Couplings via C-N and C-O Bond Activation.

Authors:  Jianyu Xu; Olivia P Bercher; Michael R Talley; Mary P Watson
Journal:  ACS Catal       Date:  2021-01-19       Impact factor: 13.084
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