Literature DB >> 19623349

Carbocyclisation of alkynes with external nucleophiles catalysed by gold, platinum and other electrophilic metals.

Shariar Md Abu Sohel1, Rai-Shung Liu.   

Abstract

This tutorial review covers recent developments in catalytic carbocyclisation of functionalised alkynes with external nucleophiles catalysed by gold, platinum and other electrophilic metals. Substrates of such reactions require a tethered functionality to react with the alkyne to complete a carbocyclic ring. We classify the reactions according to the tethered functionalities to illustrate the diversity of the carbocyclisations; these substrates include: (1) alkyne-alkyne, (2) alkyne-allene, (3) alkyne-alkene, (4) oxo-alkynes and (5) oxo-diynes and triynes. Besides their mechanistic interest, these reactions meet atom economy criteria because complex and functionalised carbocyclic products are easily assembled in a cascade sequence from readily available alkynes and nucleophiles.

Entities:  

Year:  2009        PMID： 19623349     DOI： 10.1039/b807499m

Source DB:  PubMed          Journal:  Chem Soc Rev        ISSN： 0306-0012            Impact factor:   54.564


  38 in total

1.  Au-catalyzed synthesis of 2-alkylindoles from N-arylhydroxylamines and terminal alkynes.

Authors:  Yanzhao Wang; Longwu Ye; Liming Zhang
Journal:  Chem Commun (Camb)       Date:  2011-06-03       Impact factor: 6.222

2.  The palladium catalyzed asymmetric addition of oxindoles and allenes: an atom-economical versatile method for the construction of chiral indole alkaloids.

Authors:  Barry M Trost; Jia Xie; Joshua D Sieber
Journal:  J Am Chem Soc       Date:  2011-11-30       Impact factor: 15.419

3.  The use of Br/Cl to promote regioselective gold-catalyzed rearrangement of propargylic carboxylates: an efficient synthesis of (1Z, 3E)-1-bromo/chloro-2-carboxy-1,3-dienes.

Authors:  Yanzhao Wang; Biao Lu; Liming Zhang
Journal:  Chem Commun (Camb)       Date:  2010-10-29       Impact factor: 6.222

4.  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

5.  Palladium-catalyzed carbocyclization of alkynyl ketones proceeding through a carbopalladation pathway.

Authors:  Natalia Chernyak; Serge I Gorelsky; Vladimir Gevorgyan
Journal:  Angew Chem Int Ed Engl       Date:  2011-02-07       Impact factor: 15.336

6.  Rhodium-catalyzed intra- and intermolecular [5 + 2] cycloaddition of 3-acyloxy-1,4-enyne and alkyne with concomitant 1,2-acyloxy migration.

Authors:  Xing-Zhong Shu; Xiaoxun Li; Dongxu Shu; Suyu Huang; Casi M Schienebeck; Xin Zhou; Patrick J Robichaux; Weiping Tang
Journal:  J Am Chem Soc       Date:  2012-03-12       Impact factor: 15.419

Review 7.  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

8.  Tandem Cycloisomerization/Suzuki Coupling of Arylethynyl MIDA Boronates.

Authors:  Julian M W Chan; Giovanni W Amarante; F Dean Toste
Journal:  Tetrahedron       Date:  2011-06-17       Impact factor: 2.457

9.  Tempering the reactivities of postulated α-oxo gold carbenes using bidentate ligands: implication of tricoordinated gold intermediates and the development of an expedient bimolecular assembly of 2,4-disubstituted oxazoles.

Authors:  Yingdong Luo; Kegong Ji; Yuxue Li; Liming Zhang
Journal:  J Am Chem Soc       Date:  2012-10-11       Impact factor: 15.419

10.  Gold-Catalyzed Regioselective Dimerization of Aliphatic Terminal Alkynes.

Authors:  Sheng Sun; Julien Kroll; Yingdong Luo; Liming Zhang
Journal:  Synlett       Date:  2012-01       Impact factor: 2.454
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