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Literature DB >> 23576273

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

Shuai Shi¹, Tao Wang, Weibo Yang, Matthias Rudolph, A Stephen K Hashmi.

Abstract

From terminal alkynes to glyoxals: Terminal alkynes can be oxidized under mild conditions by the use of an N-oxide in the presence of a gold catalyst. The intermediate glyoxal derivatives can be transferred in a one-pot procedure to substituted quinoxalines (see scheme).

Entities: Chemical

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Year: 2013 PMID： 23576273 DOI： 10.1002/chem.201300518

Source DB: PubMed Journal: Chemistry ISSN： 0947-6539 Impact factor: 5.236

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Cited

11 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. A Desulfonylative Approach in Oxidative Gold Catalysis: Regiospecific Access to Donor-Substituted Acyl Gold Carbenes.

Authors: Hongyi Chen; Liming Zhang
Journal: Angew Chem Int Ed Engl Date: 2015-08-12 Impact factor: 15.336

3. 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.

Authors: Jiabin Li; Kegong Ji; Renhua Zheng; Jonathan Nelson; Liming Zhang
Journal: Chem Commun (Camb) Date: 2014-04-21 Impact factor: 6.222

10. Nucleophile promoted gold redox catalysis with diazonium salts: C-Br, C-S and C-P bond formation through catalytic Sandmeyer coupling.

Authors: Haihui Peng; Rong Cai; Chang Xu; Hao Chen; Xiaodong Shi
Journal: Chem Sci Date: 2016-06-10 Impact factor: 9.825

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

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

2. A Desulfonylative Approach in Oxidative Gold Catalysis: Regiospecific Access to Donor-Substituted Acyl Gold Carbenes.

3. 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.

Review 4. Homogeneous Gold-Catalyzed Oxidation Reactions.

5. Gold(I)-Catalyzed Activation of Alkynes for the Construction of Molecular Complexity.

6. Intriguing mechanistic labyrinths in gold(I) catalysis.

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

8. A non-diazo approach to α-oxo gold carbenes via gold-catalyzed alkyne oxidation.

9. Gold(i)-catalyzed cycloisomerization of vinylidenecyclopropane-enes via carbene or non-carbene processes.

10. Nucleophile promoted gold redox catalysis with diazonium salts: C-Br, C-S and C-P bond formation through catalytic Sandmeyer coupling.