Literature DB >> 16408906

Gold(III) porphyrin-catalyzed cycloisomerization of allenones.

Cong-Ying Zhou1, Philip Wai Hong Chan, Chi-Ming Che.   

Abstract

[reaction: see text] Gold(III) porphyrin-catalyzed cycloisomerization of allenones gave the corresponding furans in good to excellent yields (up to 98%) and with quantitative substrate conversions. By recovering the Au(III) catalyst, a recyclable catalytic system is developed with over 8300 product turnovers attained for the cycloisomerization of 1-phenyl-buta-2,3-dien-1-one. The versatility of the gold(III) porphyrin catalyst was exemplified by its application to the hydroamination and hydration of phenylacetylene in 73% and 87% yield, respectively.

Entities:  

Year:  2006        PMID: 16408906     DOI: 10.1021/ol052696c

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


  18 in total

1.  Computation-guided development of Au-catalyzed cycloisomerizations proceeding via 1,2-Si or 1,2-H migrations: regiodivergent synthesis of silylfurans.

Authors:  Alexander S Dudnik; Yuanzhi Xia; Yahong Li; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2010-06-09       Impact factor: 15.419

Review 2.  Transition metal-mediated synthesis of monocyclic aromatic heterocycles.

Authors:  Anton V Gulevich; Alexander S Dudnik; Natalia Chernyak; Vladimir Gevorgyan
Journal:  Chem Rev       Date:  2013-01-10       Impact factor: 60.622

Review 3.  Stable cyclic carbenes and related species beyond diaminocarbenes.

Authors:  Mohand Melaimi; Michèle Soleilhavoup; Guy Bertrand
Journal:  Angew Chem Int Ed Engl       Date:  2010-11-15       Impact factor: 15.336

4.  Serendipitous discovery of the catalytic hydroammoniumation and methylamination of alkynes.

Authors:  Xiaoming Zeng; Rei Kinjo; Bruno Donnadieu; Guy Bertrand
Journal:  Angew Chem Int Ed Engl       Date:  2010       Impact factor: 15.336

5.  A cationic gold(I) complex as a general catalyst for the intermolecular hydroamination of alkynes: application to the one-pot synthesis of allenes from two alkynes and a sacrificial amine.

Authors:  Xiaoming Zeng; Guido D Frey; Shazia Kousar; Guy Bertrand
Journal:  Chemistry       Date:  2009       Impact factor: 5.236

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

Authors:  David V Partyka; Thomas J Robilotto; Matthias Zeller; Allen D Hunter; Thomas G Gray
Journal:  Proc Natl Acad Sci U S A       Date:  2008-09-09       Impact factor: 11.205

7.  Synthesis of a simplified version of stable bulky and rigid cyclic (alkyl)(amino)carbenes, and catalytic activity of the ensuing gold(I) complex in the three-component preparation of 1,2-dihydroquinoline derivatives.

Authors:  Xiaoming Zeng; Guido D Frey; Rei Kinjo; Bruno Donnadieu; Guy Bertrand
Journal:  J Am Chem Soc       Date:  2009-06-24       Impact factor: 15.419

8.  Metal-catalyzed 1,2-shift of diverse migrating groups in allenyl systems as a new paradigm toward densely functionalized heterocycles.

Authors:  Alexander S Dudnik; Anna W Sromek; Marina Rubina; Joseph T Kim; Alexander V Kel'in; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2008-01-04       Impact factor: 15.419

9.  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

10.  Mechanistic insights into the gold-catalyzed cycloisomerization of bromoallenyl ketones: ligand-controlled regioselectivity.

Authors:  Yuanzhi Xia; Alexander S Dudnik; Vladimir Gevorgyan; Yahong Li
Journal:  J Am Chem Soc       Date:  2008-05-08       Impact factor: 15.419

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