Literature DB >> 25115858

Synthesis of α-aryl esters and nitriles: deaminative coupling of α-aminoesters and α-aminoacetonitriles with arylboronic acids.

Guojiao Wu1, Yifan Deng, Chaoqiang Wu, Yan Zhang, Jianbo Wang.   

Abstract

Transition-metal-free synthesis of α-aryl esters and nitriles using arylboronic acids with α-aminoesters and α-aminoacetonitriles, respectively, as the starting materials has been developed. The reaction represents a rare case of converting C(sp(3))-N bonds into C(sp(3))-C(sp(2)) bonds. The reaction conditions are mild, demonstrate good functional-group tolerance, and can be scaled up.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  arenes; boron; diazo compounds; nitriles; synthetic methods

Year:  2014        PMID: 25115858     DOI: 10.1002/anie.201406765

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  10 in total

1.  Deaminative Arylation of Amino Acid-derived Pyridinium Salts.

Authors:  Megan E Hoerrner; Kristen M Baker; Corey H Basch; Earl M Bampo; Mary P Watson
Journal:  Org Lett       Date:  2019-08-29       Impact factor: 6.005

2.  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

3.  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

4.  Rh(II)-Catalyzed Reactions of Diazoesters with Organozinc Reagents.

Authors:  Robert Panish; Ramajeyam Selvaraj; Joseph M Fox
Journal:  Org Lett       Date:  2015-08-04       Impact factor: 6.005

5.  An intramolecular coupling approach to alkyl bioisosteres for the synthesis of multisubstituted bicycloalkyl boronates.

Authors:  Yangyang Yang; Jet Tsien; Jonathan M E Hughes; Byron K Peters; Rohan R Merchant; Tian Qin
Journal:  Nat Chem       Date:  2021-09-28       Impact factor: 24.427

6.  A multicomponent approach for the preparation of homoallylic alcohols.

Authors:  Jian-Siang Poh; Shing-Hing Lau; Iain G Dykes; Duc N Tran; Claudio Battilocchio; Steven V Ley
Journal:  Chem Sci       Date:  2016-07-08       Impact factor: 9.825

7.  Flow chemistry as a discovery tool to access sp2-sp3 cross-coupling reactions via diazo compounds.

Authors:  Duc N Tran; Claudio Battilocchio; Shing-Bong Lou; Joel M Hawkins; Steven V Ley
Journal:  Chem Sci       Date:  2014-11-07       Impact factor: 9.825

8.  Passerini-type reaction of boronic acids enables α-hydroxyketones synthesis.

Authors:  Kai Yang; Feng Zhang; Tongchang Fang; Chaokun Li; Wangyang Li; Qiuling Song
Journal:  Nat Commun       Date:  2021-01-19       Impact factor: 14.919

9.  Photocatalytic acyl azolium-promoted alkoxycarbonylation of trifluoroborates.

Authors:  Joshua L Zhu; Karl A Scheidt
Journal:  Tetrahedron       Date:  2021-06-16       Impact factor: 2.388

10.  Transition metal-free direct dehydrogenative arylation of activated C(sp3)-H bonds: synthetic ambit and DFT reactivity predictions.

Authors:  Kaitlyn Lovato; Lirong Guo; Qing-Long Xu; Fengting Liu; Muhammed Yousufuddin; Daniel H Ess; László Kürti; Hongyin Gao
Journal:  Chem Sci       Date:  2018-08-27       Impact factor: 9.825

  10 in total

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