Literature DB >> 28613864

Regio- and Stereospecific Copper-Catalyzed Substitution Reaction of Propargylic Ammonium Salts with Aryl Grignard Reagents.

Manuel Guisán-Ceinos1, Victor Martín-Heras1, Mariola Tortosa1,2.   

Abstract

We have developed a copper-catalyzed substitution reaction of propargylic ammonium salts with aryl Grignard reagents. The reaction is stereospecific and α-regioselective and proceeds with exceptional functional group tolerance. Conveniently, a stable, inexpensive, and commercially available copper salt is used and no added ligand is required.

Entities:  

Year:  2017        PMID： 28613864     DOI： 10.1021/jacs.7b05273

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


  7 in total

1.  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

2.  Enantioselective and Diastereodivergent Allylation of Propargylic C-H Bonds.

Authors:  Jin Zhu; Yidong Wang; Aaron D Charlack; Yi-Ming Wang
Journal:  J Am Chem Soc       Date:  2022-08-17       Impact factor: 16.383

3.  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

4.  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

5.  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

6.  Stereospecific and Chemoselective Copper-Catalyzed Deaminative Silylation of Benzylic Ammonium Triflates.

Authors:  Jonas Scharfbier; Benjamin M Gross; Martin Oestreich
Journal:  Angew Chem Int Ed Engl       Date:  2019-12-04       Impact factor: 15.336

7.  Copper-catalyzed enantioselective Sonogashira-type oxidative cross-coupling of unactivated C(sp3)-H bonds with alkynes.

Authors:  Zhen-Hua Zhang; Xiao-Yang Dong; Xuan-Yi Du; Qiang-Shuai Gu; Zhong-Liang Li; Xin-Yuan Liu
Journal:  Nat Commun       Date:  2019-12-12       Impact factor: 14.919
  7 in total

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