Literature DB >> 24622909

Expanding the horizon of intermolecular trapping of in situ generated α-oxo gold carbenes: efficient oxidative union of allylic sulfides and terminal alkynes via C-C bond formation.

Jiabin Li1,2, Kegong Ji1, Renhua Zheng1, Jonathan Nelson1, Liming Zhang1.   

Abstract

With a new P,S-bidentate phosphine as the ligand to gold(I), the α-oxo gold carbenes generated in situ via gold-catalyzed intermolecular oxidation of terminal alkynes were effectively trapped by various allylic sulfides, resulting in the formation of α-aryl(alkyl)thio-γ,δ-unsaturated ketones upon facile [2,3]sigmatropic rearrangements.

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Year:  2014        PMID： 24622909      PMCID： PMC4090113          DOI： 10.1039/c4cc00739e

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  34 in total

1.  Gold-catalyzed oxidative cyclization of 1,5-enynes using external oxidants.

Authors:  Dhananjayan Vasu; Hsiao-Hua Hung; Sabyasachi Bhunia; Sagar Ashok Gawade; Arindam Das; Rai-Shung Liu
Journal:  Angew Chem Int Ed Engl       Date:  2011-06-06       Impact factor: 15.336

2.  An efficient [2 + 2 + 1] synthesis of 2,5-disubstituted oxazoles via gold-catalyzed intermolecular alkyne oxidation.

Authors:  Weimin He; Chaoqun Li; Liming Zhang
Journal:  J Am Chem Soc       Date:  2011-05-12       Impact factor: 15.419

3.  Alkynes as equivalents of alpha-diazo ketones in generating alpha-oxo metal carbenes: a gold-catalyzed expedient synthesis of dihydrofuran-3-ones.

Authors:  Longwu Ye; Li Cui; Guozhu Zhang; Liming Zhang
Journal:  J Am Chem Soc       Date:  2010-03-17       Impact factor: 15.419

4.  Gold-catalyzed rearrangement of allylic oxonium ylides: efficient synthesis of highly functionalized dihydrofuran-3-ones.

Authors:  Junkai Fu; Hai Shang; Zhaofeng Wang; Le Chang; Wenbing Shao; Zhen Yang; Yefeng Tang
Journal:  Angew Chem Int Ed Engl       Date:  2013-03-06       Impact factor: 15.336

5.  Gold-catalyzed reactions between alkenyldiazo carbonyl species and acetals.

Authors:  Vinayak Vishnu Pagar; Appaso M Jadhav; Rai-Shung Liu
Journal:  J Org Chem       Date:  2013-05-14       Impact factor: 4.354

6.  Optimizing P,N-bidentate ligands for oxidative gold catalysis: efficient intermolecular trapping of α-oxo gold carbenes by carboxylic acids.

Authors:  Kegong Ji; Yulong Zhao; Liming Zhang
Journal:  Angew Chem Int Ed Engl       Date:  2013-05-02       Impact factor: 15.336

7.  Biarylphosphonite gold(I) complexes as superior catalysts for oxidative cyclization of propynyl arenes into indan-2-ones.

Authors:  Guilhem Henrion; Thomas E J Chavas; Xavier Le Goff; Fabien Gagosz
Journal:  Angew Chem Int Ed Engl       Date:  2013-05-06       Impact factor: 15.336

8.  Gold-catalyzed synthesis of glyoxals by oxidation of terminal alkynes: one-pot synthesis of quinoxalines.

Authors:  Shuai Shi; Tao Wang; Weibo Yang; Matthias Rudolph; A Stephen K Hashmi
Journal:  Chemistry       Date:  2013-04-09       Impact factor: 5.236

9.  Gold-catalyzed oxidative rearrangement of homopropargylic ether via oxonium ylide.

Authors:  Mei Xu; Tian-Tian Ren; Chuan-Ying Li
Journal:  Org Lett       Date:  2012-09-06       Impact factor: 6.005

10.  Gold-catalyzed regioselective oxidation of propargylic carboxylates: a reliable access to α-carboxy-α,β-unsaturated ketones/aldehydes.

Authors:  Kegong Ji; Jonathan Nelson; Liming Zhang
Journal:  Beilstein J Org Chem       Date:  2013-09-24       Impact factor: 2.883
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  7 in total

1.  Enantioselective oxidative gold catalysis enabled by a designed chiral P,N-bidentate ligand.

Authors:  Kegong Ji; Zhitong Zheng; Zhixun Wang; Liming Zhang
Journal:  Angew Chem Int Ed Engl       Date:  2014-11-27       Impact factor: 15.336

2.  Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts.

Authors:  Daniel Kaiser; Immo Klose; Rik Oost; James Neuhaus; Nuno Maulide
Journal:  Chem Rev       Date:  2019-06-25       Impact factor: 60.622

3.  Facile synthesis of α-alkoxyl amides via scandium-catalyzed oxidative reaction between ynamides and alcohols.

Authors:  Zhi-Xin Zhang; Bo-Han Zhu; Pei-Xi Xie; Jia-Qi Tang; Xin-Ling Li; Chunyin Zhu; Ying-Wu Yin; Long-Wu Ye
Journal:  RSC Adv       Date:  2018-05-18       Impact factor: 4.036

4.  Gold-Catalyzed Oxidation of Propargylic Ethers with Internal C-C Triple Bonds: Impressive Regioselectivity Enabled by Inductive Effect.

Authors:  Kegong Ji; Brendan D'Souza; Jon Nelson; Liming Zhang
Journal:  J Organomet Chem       Date:  2014-11-01       Impact factor: 2.369

Review 5.  Homogeneous Gold-Catalyzed Oxidation Reactions.

Authors:  Zhitong Zheng; Xu Ma; Xinpeng Cheng; Ke Zhao; Kaylaa Gutman; Tianyou Li; Liming Zhang
Journal:  Chem Rev       Date:  2021-02-16       Impact factor: 72.087

Review 6.  Sulfur-Based Ylides in Transition-Metal-Catalysed Processes.

Authors:  James D Neuhaus; Rik Oost; Jérémy Merad; Nuno Maulide
Journal:  Top Curr Chem (Cham)       Date:  2018-04-13

7.  Atom-economic generation of gold carbenes: gold-catalyzed formal [3+2] cycloaddition between ynamides and isoxazoles.

Authors:  Ai-Hua Zhou; Qiao He; Chao Shu; Yong-Fei Yu; Shuang Liu; Tian Zhao; Wei Zhang; Xin Lu; Long-Wu Ye
Journal:  Chem Sci       Date:  2014-11-12       Impact factor: 9.825
  7 in total

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