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Literature DB >> 16756286

Synthesis of aromatic ketones by a transition metal-catalyzed tandem sequence.

Jing Zhao¹, Colin O Hughes, F Dean Toste.

Abstract

Both simple Ag(I) and Au(I) are effective catalysts for a tandem [3,3]-sigmatropic rearrangement/formal Myers-Saito cyclization of propargyl esters to form aromatic ketones. A mechanism in which the metal catalyzes both of these processes through alkyne activation is proposed. By using this method a wide range of aromatic structures including naphthyl, anthracenyl and indole ketones are available from readily available propargyl esters.

Entities: Chemical

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Year: 2006 PMID： 16756286 DOI： 10.1021/ja061942s

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

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Cited

22 in total

1. Gold-catalyzed cycloisomerization of 1,5-allenynes via dual activation of an ene reaction.

Authors: Paul Ha-Yeon Cheong; Philip Morganelli; Michael R Luzung; K N Houk; F Dean Toste
Journal: J Am Chem Soc Date: 2008-03-08 Impact factor: 15.419

2. Rhodium-catalyzed ring expansion of cyclopropanes to seven-membered rings by 1,5 C-C bond migration.

Authors: Xiaoxun Li; Min Zhang; Dongxu Shu; Patrick J Robichaux; Suyu Huang; Weiping Tang
Journal: Angew Chem Int Ed Engl Date: 2011-09-09 Impact factor: 15.336

3. Substituent Effect on the Formation and Their Reactivity of Platinum Carbenoids.

Authors: Eun Jin Cho; Daesung Lee
Journal: Adv Synth Catal Date: 2008-11-17 Impact factor: 5.837

4. Synthesis of highly functionalized cyclohexenone rings: rhodium-catalyzed 1,3-acyloxy migration and subsequent [5+1] cycloaddition.

Authors: Dongxu Shu; Xiaoxun Li; Min Zhang; Patrick J Robichaux; Weiping Tang
Journal: Angew Chem Int Ed Engl Date: 2010-12-29 Impact factor: 15.336

10. Mechanistically diverse copper-, silver-, and gold-catalyzed acyloxy and phosphatyloxy migrations: efficient synthesis of heterocycles via cascade migration/cycloisomerization approach.

Authors: Todd Schwier; Anna W Sromek; Dahrika M L Yap; Dmitri Chernyak; Vladimir Gevorgyan
Journal: J Am Chem Soc Date: 2007-07-21 Impact factor: 15.419

Synthesis of aromatic ketones by a transition metal-catalyzed tandem sequence.

1. Gold-catalyzed cycloisomerization of 1,5-allenynes via dual activation of an ene reaction.

2. Rhodium-catalyzed ring expansion of cyclopropanes to seven-membered rings by 1,5 C-C bond migration.

3. Substituent Effect on the Formation and Their Reactivity of Platinum Carbenoids.

4. Synthesis of highly functionalized cyclohexenone rings: rhodium-catalyzed 1,3-acyloxy migration and subsequent [5+1] cycloaddition.

5. Indole synthesis: a review and proposed classification.

6. Gold-catalyzed transannular [4+3] cycloaddition reactions.

7. A porphyrin complex of gold(I): (phosphine)gold(I) azides as cation precursors.

8. Mechanistic studies on Au(I)-catalyzed [3,3]-sigmatropic rearrangements using cyclopropane probes.

9. Rh(I)-catalyzed cyclocarbonylation of allenol esters to prepare acetoxy 4-alkylidenecyclopent-3-en-2-ones.

10. Mechanistically diverse copper-, silver-, and gold-catalyzed acyloxy and phosphatyloxy migrations: efficient synthesis of heterocycles via cascade migration/cycloisomerization approach.