Literature DB >> 16548035

Ring-closing metathesis as a basis for the construction of aromatic compounds.

Timothy J Donohoe1, Allan J Orr, Matilda Bingham.   

Abstract

The use of metathesis, especially in the context of ring-closing metathesis (RCM) to form five- and six-membered rings, is widespread in organic chemistry today. However, there are surprisingly few examples of the reaction being used to form aromatic compounds. The central place of aromatic compounds in both medicinal chemistry and natural products synthesis, coupled with the efficiency and functional group tolerance of RCM catalysts, means that there is now an interesting opportunity to use RCM for the synthesis of arenes. Although the formation of an aromatic compound was viewed in many early examples as an undesirable degradation product, several rationally designed methods towards the preparation of aromatic compounds by RCM have recently been developed.

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Year:  2006        PMID: 16548035     DOI: 10.1002/anie.200503512

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  12 in total

Review 1.  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

2.  Olefin cross-metathesis-based approaches to furans: procedures for the preparation of di- and trisubstituted variants.

Authors:  Timothy J Donohoe; John F Bower; José A Basutto
Journal:  Nat Protoc       Date:  2010-12-02       Impact factor: 13.491

3.  An expedient route to substituted furans via olefin cross-metathesis.

Authors:  Timothy J Donohoe; John F Bower
Journal:  Proc Natl Acad Sci U S A       Date:  2010-02-08       Impact factor: 11.205

4.  Synthesis of N-heterocyclic carbene ligands and derived ruthenium olefin metathesis catalysts.

Authors:  Xavier Bantreil; Steven P Nolan
Journal:  Nat Protoc       Date:  2010-12-16       Impact factor: 13.491

5.  Polycyclic Aromatic Hydrocarbons via Iron(III)-Catalyzed Carbonyl-Olefin Metathesis.

Authors:  Christopher C McAtee; Paul S Riehl; Corinna S Schindler
Journal:  J Am Chem Soc       Date:  2017-02-21       Impact factor: 15.419

6.  Synthesis of polycyclic benzofused nitrogen heterocycles via a tandem ynamide benzannulation/ring-closing metathesis strategy. Application in a formal total synthesis of (+)-FR900482.

Authors:  Xiao Yin Mak; Aimee L Crombie; Rick L Danheiser
Journal:  J Org Chem       Date:  2011-02-15       Impact factor: 4.354

7.  A 1,3-dihydro-1,3-azaborine debuts.

Authors:  Senmiao Xu; Lev N Zakharov; Shih-Yuan Liu
Journal:  J Am Chem Soc       Date:  2011-11-21       Impact factor: 15.419

8.  Thermodynamic synthesis of solution processable ladder polymers.

Authors:  Jongbok Lee; Bharath Bangalore Rajeeva; Tianyu Yuan; Zi-Hao Guo; Yen-Hao Lin; Mohammed Al-Hashimi; Yuebing Zheng; Lei Fang
Journal:  Chem Sci       Date:  2015-11-06       Impact factor: 9.825

9.  De novo synthesis of multisubstituted aryl amines using alkene cross metathesis.

Authors:  Matthew R Tatton; Iain Simpson; Timothy J Donohoe
Journal:  Org Lett       Date:  2014-03-19       Impact factor: 6.005

10.  Z-Selective olefin metathesis on peptides: investigation of side-chain influence, preorganization, and guidelines in substrate selection.

Authors:  Shane L Mangold; Daniel J O'Leary; Robert H Grubbs
Journal:  J Am Chem Soc       Date:  2014-08-20       Impact factor: 15.419

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