Literature DB >> 32685767

Regio- and Stereoselective Synthesis of 1,2-Dihaloalkenes Using In-Situ-Generated ICl, IBr, BrCl, I2, and Br2.

Xiaojun Zeng1, Shiwen Liu2, Yuhao Yang1, Yi Yang2, Gerald B Hammond1,3, Bo Xu2.   

Abstract

We describe a catalyst-free 1,2-trans-dihalogenation of alkynes with an unprecedented substrate scope and exclusive regio- and stereoselectivity. This versatile dihalogenation system-a combination of NX1S electrophile and alkali metal halide (MX2) in acetic acid-is applicable for diverse categories of alkynes (electron-rich or poor alkynes, internal and terminal alkynes, or heteroatoms such as O-, N-, S-substituted alkynes). The hydrogen bonding donor solvent acetic acid is essential for the in-situ generation of X1X2 electrophile, including ICl, IBr, BrCl, I2, and Br2.

Entities:  

Year:  2020        PMID： 32685767      PMCID： PMC7367077          DOI： 10.1016/j.chempr.2020.03.011

Source DB:  PubMed          Journal:  Chem            Impact factor:   22.804


  48 in total

1.  Construction of beta-haloenamides via direct copper-promoted coupling of lactams with 2-chloro and 2-bromo vinyliodides.

Authors:  Cuixiang Sun; Jason E Camp; Steven M Weinreb
Journal:  Org Lett       Date:  2006-04-27       Impact factor: 6.005

2.  Organocatalytic asymmetric synthesis of versatile gamma-lactams.

Authors:  Thomas B Poulsen; Gustav Dickmeiss; Jacob Overgaard; Karl Anker Jørgensen
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

3.  From meiogynin A to the synthesis of dual inhibitors of Bcl-xL and Mcl-1 anti-apoptotic proteins.

Authors:  S Desrat; C Remeur; C Gény; G Rivière; C Colas; V Dumontet; N Birlirakis; B I Iorga; F Roussi
Journal:  Chem Commun (Camb)       Date:  2014-08-11       Impact factor: 6.222

4.  Metal-Free Transfer Hydroiodination of C-C Multiple Bonds.

Authors:  Weiqiang Chen; Johannes C L Walker; Martin Oestreich
Journal:  J Am Chem Soc       Date:  2018-12-28       Impact factor: 15.419

5.  Highly Regio- and Diastereoselective Formation of Tetrasubstituted (Z)-1,2-Dihaloalkenes from the Halogenation of Trimethylsilyl Alkynes with ICl.

Authors:  Kyle C Sproul; Wesley A Chalifoux
Journal:  Org Lett       Date:  2015-06-24       Impact factor: 6.005

Review 6.  Enzymatic Halogenation and Dehalogenation Reactions: Pervasive and Mechanistically Diverse.

Authors:  Vinayak Agarwal; Zachary D Miles; Jaclyn M Winter; Alessandra S Eustáquio; Abrahim A El Gamal; Bradley S Moore
Journal:  Chem Rev       Date:  2017-01-20       Impact factor: 60.622

7.  Clean inversion of configuration in the Pd-catalyzed cross-coupling of 2-bromo-1,3-dienes.

Authors:  Xingzhong Zeng; Qian Hu; Mingxing Qian; Ei-ichi Negishi
Journal:  J Am Chem Soc       Date:  2003-11-12       Impact factor: 15.419

Review 8.  The organometallic fluorine chemistry of palladium and rhodium: studies toward aromatic fluorination.

Authors:  Vladimir V Grushin
Journal:  Acc Chem Res       Date:  2010-01-19       Impact factor: 22.384

9.  Successive copper(I)-catalyzed cross-couplings in one pot: a novel and efficient starting point for synthesis of carbapenems.

Authors:  Biao Jiang; Hua Tian; Zuo-Gang Huang; Min Xu
Journal:  Org Lett       Date:  2008-05-30       Impact factor: 6.005

10.  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
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  1 in total

1.  Regio- and stereoselective thiocyanatothiolation of alkynes and alkenes by using NH4SCN and N-thiosuccinimides.

Authors:  Liang Qi; Shiwen Liu; Linxia Xiao
Journal:  RSC Adv       Date:  2020-09-10       Impact factor: 4.036
  1 in total

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