Literature DB >> 19444849

Regio- and stereoselective generation of alkenylindium compounds from indium tribromide, alkynes, and ketene silyl acetals.

Yoshihiro Nishimoto1, Ryosuke Moritoh, Makoto Yasuda, Akio Baba.   

Abstract

InBr(3) promotes the addition of ketene silyl acetals to monosubstituted alkynes to afford 2,2-disubstituted alkenylindium compounds in high regio- and stereoselectivity (see scheme). In addition, the alkenylindium derivatives have been subsequently coupled with iodobenzene in the presence of a palladium catalyst.

Entities:  

Year:  2009        PMID: 19444849     DOI: 10.1002/anie.200901417

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


  6 in total

1.  Silver catalyzed proto- and sila-Nakamura-type α-vinylation of silyl enol ethers with dichloroacetylene. Divergent formation of stereochemically pure tri- and tetrasubstituted olefins.

Authors:  Lun Li; Kimberly A Wasik; Brian J Frost; Laina M Geary
Journal:  Tetrahedron Lett       Date:  2019-11-06       Impact factor: 2.415

2.  A Catalytic Intermolecular Formal Ene Reaction between Ketone-Derived Silyl Enol Ethers and Alkynes.

Authors:  Stephen D Holmbo; Nicole A Godfrey; Joshua J Hirner; Sergey V Pronin
Journal:  J Am Chem Soc       Date:  2016-09-16       Impact factor: 15.419

3.  A Concise Approach to Paxilline Indole Diterpenes.

Authors:  David T George; Eric J Kuenstner; Sergey V Pronin
Journal:  J Am Chem Soc       Date:  2015-12-07       Impact factor: 15.419

4.  Regio- and Stereoselective Allylindation of Alkynes Using InBr₃ and Allylic Silanes: Synthesis, Characterization, and Application of 1,4-Dienylindiums toward Skipped Dienes.

Authors:  Yoshihiro Nishimoto; Junyi Yi; Tatsuaki Takata; Akio Baba; Makoto Yasuda
Journal:  Molecules       Date:  2018-07-27       Impact factor: 4.411

Review 5.  Indole diterpenoid natural products as the inspiration for new synthetic methods and strategies.

Authors:  Michael A Corsello; Junyong Kim; Neil K Garg
Journal:  Chem Sci       Date:  2017-06-27       Impact factor: 9.825

6.  Selective oxymetalation of terminal alkynes via 6-endo cyclization: mechanistic investigation and application to the efficient synthesis of 4-substituted isocoumarins.

Authors:  Yuji Kita; Tetsuji Yata; Yoshihiro Nishimoto; Kouji Chiba; Makoto Yasuda
Journal:  Chem Sci       Date:  2018-06-15       Impact factor: 9.825

  6 in total

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