Literature DB >> 19385654

Iridium-catalyzed addition of acid chlorides to terminal alkynes.

Tomohiro Iwai1, Tetsuaki Fujihara, Jun Terao, Yasushi Tsuji.   

Abstract

An iridium N-heterocyclic carbene (NHC) complex, IrCl(cod)(IPr), successfully catalyzed an addition of common aromatic acid chlorides to terminal alkynes to afford (Z)-beta-chloro-alpha,beta-unsaturated ketones regio- and stereoselectively. When the NHC ligand (IPr) was changed to a phosphine (RuPhos), the addition occurred with decarbonylation to give the corresponding (Z)-vinyl chlorides. Furthermore, the former reaction using IrCl(cod)(IPr) can be applied to the catalytic synthesis of 2,5-disubstituted furans.

Entities:  

Year:  2009        PMID: 19385654     DOI: 10.1021/ja901778y

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


  7 in total

1.  Stereoselective Synthesis of Trisubstituted Vinyl Bromides by Addition of Alkynes to Oxocarbenium Ions.

Authors:  Andrew R Ehle; Melissa G Morris; Bryan D Klebon; Glenn P A Yap; Mary P Watson
Journal:  Synlett       Date:  2015-09-14       Impact factor: 2.454

2.  An oxidation of benzyl methyl ethers with nbs that selectively affords either aromatic aldehydes or aromatic methyl esters.

Authors:  Abdelrahman S Mayhoub; Arindam Talukdar; Mark Cushman
Journal:  J Org Chem       Date:  2010-05-21       Impact factor: 4.354

3.  Decarbonylative Suzuki-Miyaura Cross-Coupling of Aroyl Chlorides.

Authors:  Tongliang Zhou; Pei-Pei Xie; Chong-Lei Ji; Xin Hong; Michal Szostak
Journal:  Org Lett       Date:  2020-08-10       Impact factor: 6.005

4.  Metal-free, Regio-, and Stereo-Controlled Hydrochlorination and Hydrobromination of Ynones and Ynamides.

Authors:  Xiaojun Zeng; Zhichao Lu; Shiwen Liu; Gerald B Hammond; Bo Xu
Journal:  J Org Chem       Date:  2017-12-07       Impact factor: 4.354

5.  Chloride-Tolerant Gold(I)-Catalyzed Regioselective Hydrochlorination of Alkynes.

Authors:  Rene Ebule; Shengzong Liang; Gerald B Hammond; Bo Xu
Journal:  ACS Catal       Date:  2017-09-07       Impact factor: 13.084

6.  Iridium-Catalyzed Hydrochlorination and Hydrobromination of Alkynes by Shuttle Catalysis.

Authors:  Peng Yu; Alessandro Bismuto; Bill Morandi
Journal:  Angew Chem Int Ed Engl       Date:  2020-01-16       Impact factor: 15.336

7.  One-Pot Synthesis of (Z)-β-Halovinyl Ketones via the Cascade of Sonogashira Coupling and Hydrohalogenation.

Authors:  Fa-Jie Chen; Zhenguo Hua; Jianhui Chen; Jiajia Chen; Daesung Lee; Yuanzhi Xia
Journal:  Front Chem       Date:  2021-04-22       Impact factor: 5.221

  7 in total

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