Literature DB >> 17887766

Palladium-catalyzed alpha-vinylation of carbonyl compounds.

Jinkun Huang1, Emilio Bunel, Margaret M Faul.   

Abstract

A mild, general, catalytic system for the alpha-vinylation of carbonyl compounds has been developed. By employing [Pd(P(t)Bu(3))Br](2) as catalyst and LHMDS as base, vinyl bromides, vinyl triflates, and vinyl tosylates couple with 3-methyloxindole in satisfactory yields. The same catalytic system is extended to the alpha-vinylation of ketones and esters.

Entities:  

Year:  2007        PMID： 17887766     DOI： 10.1021/ol7019839

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  10 in total

1.  Palladium-Catalyzed Selective α-Alkenylation of Pyridylmethyl Ethers with Vinyl Bromides.

Authors:  Xiaodong Yang; Byeong-Seon Kim; Minyan Li; Patrick J Walsh
Journal:  Org Lett       Date:  2016-05-10       Impact factor: 6.005

2.  Mizoroki-Heck Cyclizations of Amide Derivatives for the Introduction of Quaternary Centers.

Authors:  Jose M Medina; Jesus Moreno; Sophie Racine; Shuaijing Du; Neil K Garg
Journal:  Angew Chem Int Ed Engl       Date:  2017-05-03       Impact factor: 15.336

3.  Selective monoarylation of acetate esters and aryl methyl ketones using aryl chlorides.

Authors:  Mark R Biscoe; Stephen L Buchwald
Journal:  Org Lett       Date:  2009-04-16       Impact factor: 6.005

4.  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

5.  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

6.  Orthogonal Pd- and Cu-based catalyst systems for C- and N-arylation of oxindoles.

Authors:  Ryan A Altman; Alan M Hyde; Xiaohua Huang; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2008-06-28       Impact factor: 15.419

7.  Palladium-Catalyzed Decarbonylative Dehydration for the Synthesis of α-Vinyl Carbonyl Compounds and Total Synthesis of (-)-Aspewentins A, B, and C.

Authors:  Yiyang Liu; Scott C Virgil; Robert H Grubbs; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2015-07-29       Impact factor: 15.336

8.  Palladium-catalyzed enantioselective alpha-arylation and alpha-vinylation of oxindoles facilitated by an axially chiral P-stereogenic ligand.

Authors:  Alexander M Taylor; Ryan A Altman; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2009-07-29       Impact factor: 15.419

9.  Total synthesis of the strychnos alkaloid (+)-minfiensine: tandem enantioselective intramolecular Heck-iminium ion cyclization.

Authors:  Amy B Dounay; Philip G Humphreys; Larry E Overman; Aaron D Wrobleski
Journal:  J Am Chem Soc       Date:  2008-02-28       Impact factor: 15.419

10.  Alkenylation of C(sp3 )-H Bonds by Zincation/Copper-Catalyzed Cross-Coupling with Iodonium Salts.

Authors:  Chuan Liu; Qiu Wang
Journal:  Angew Chem Int Ed Engl       Date:  2018-03-15       Impact factor: 15.336
  10 in total

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