Literature DB >> 21692488

Rh-catalyzed transannulation of N-tosyl-1,2,3-triazoles with terminal alkynes.

Buddhadeb Chattopadhyay1, Vladimir Gevorgyan.   

Abstract

The first transannulation of 1,2,3-triazoles with terminal alkynes into pyrroles is reported. The reaction proceeds in the presence of a Rh(2)(oct)(4)/AgOCOCF(3) binary catalyst system providing a straightforward approach to 1,2,4-trisubstituted pyrroles in good to excellent yields.
© 2011 American Chemical Society

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Year:  2011        PMID： 21692488      PMCID： PMC3156790          DOI： 10.1021/ol2014347

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


  11 in total

1.  Nickel-catalyzed regio- and enantioselective annulation reactions of 1,2,3,4-benzothiatriazine-1,1(2H)-dioxides with allenes.

Authors:  Tomoya Miura; Motoshi Yamauchi; Akira Kosaka; Masahiro Murakami
Journal:  Angew Chem Int Ed Engl       Date:  2010-07-05       Impact factor: 15.336

2.  Rh-catalyzed transannulation of pyridotriazoles with alkynes and nitriles.

Authors:  Stepan Chuprakov; Frank W Hwang; Vladimir Gevorgyan
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

3.  Copper-catalyzed synthesis of N-sulfonyl-1,2,3-triazoles: controlling selectivity.

Authors:  Eun Jeong Yoo; Mårten Ahlquist; Seok Hwan Kim; Imhyuck Bae; Valery V Fokin; K Barry Sharpless; Sukbok Chang
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

4.  Palladium-catalyzed denitrogenation reaction of 1,2,3-benzotriazin-4(3H)-ones incorporating isocyanides.

Authors:  Tomoya Miura; Yui Nishida; Masao Morimoto; Motoshi Yamauchi; Masahiro Murakami
Journal:  Org Lett       Date:  2011-02-14       Impact factor: 6.005

5.  Catalytic asymmetric cyclopropanation of heteroaryldiazoacetates.

Authors:  H M Davies; R J Townsend
Journal:  J Org Chem       Date:  2001-10-05       Impact factor: 4.354

6.  Synthesis and reactivity of rhodium(II) N-triflyl azavinyl carbenes.

Authors:  Neil Grimster; Li Zhang; Valery V Fokin
Journal:  J Am Chem Soc       Date:  2010-03-03       Impact factor: 15.419

7.  Rhodium-catalyzed transannulation of 1,2,3-triazoles with nitriles.

Authors:  Tony Horneff; Stepan Chuprakov; Natalia Chernyak; Vladimir Gevorgyan; Valery V Fokin
Journal:  J Am Chem Soc       Date:  2008-10-15       Impact factor: 15.419

8.  Nickel-catalysed denitrogenative alkyne insertion reactions of N-sulfonyl-1,2,3-triazoles.

Authors:  Tomoya Miura; Motoshi Yamauchi; Masahiro Murakami
Journal:  Chem Commun (Camb)       Date:  2009-01-06       Impact factor: 6.222

9.  Palladium-catalyzed indolization of N-aroylbenzotriazoles with disubstituted alkynes.

Authors:  Itaru Nakamura; Tetsuya Nemoto; Naozumi Shiraiwa; Masahiro Terada
Journal:  Org Lett       Date:  2009-03-05       Impact factor: 6.005

10.  Synthesis of 1(2H)-isoquinolones by the nickel-catalyzed denitrogenative alkyne insertion of 1,2,3-benzotriazin-4(3H)-ones.

Authors:  Tomoya Miura; Motoshi Yamauchi; Masahiro Murakami
Journal:  Org Lett       Date:  2008-06-18       Impact factor: 6.005
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  19 in total

Review 1.  Transition-metal-catalyzed denitrogenative transannulation: converting triazoles into other heterocyclic systems.

Authors:  Buddhadeb Chattopadhyay; Vladimir Gevorgyan
Journal:  Angew Chem Int Ed Engl       Date:  2011-11-25       Impact factor: 15.336

2.  A new reactivity mode for the diazo group: diastereoselective 1,3-aminoalkylation reaction of β-amino-α-diazoesters to give triazolines.

Authors:  Alexey Kuznetsov; Anton V Gulevich; Donald J Wink; Vladimir Gevorgyan
Journal:  Angew Chem Int Ed Engl       Date:  2014-07-01       Impact factor: 15.336

Review 3.  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

4.  Versatile reactivity of rhodium-iminocarbenes derived from N-sulfonyl triazoles.

Authors:  Anton V Gulevich; Vladimir Gevorgyan
Journal:  Angew Chem Int Ed Engl       Date:  2013-01-07       Impact factor: 15.336

5.  Ring expansion and rearrangements of rhodium(II) azavinyl carbenes.

Authors:  Nicklas Selander; Brady T Worrell; Valery V Fokin
Journal:  Angew Chem Int Ed Engl       Date:  2012-11-19       Impact factor: 15.336

6.  Rhodium-catalyzed NH insertion of pyridyl carbenes derived from pyridotriazoles: a general and efficient approach to 2-picolylamines and imidazo[1,5-a]pyridines.

Authors:  Yi Shi; Anton V Gulevich; Vladimir Gevorgyan
Journal:  Angew Chem Int Ed Engl       Date:  2014-10-21       Impact factor: 15.336

7.  Expedient synthesis of fused azepine derivatives using a sequential rhodium(II)-catalyzed cyclopropanation/1-aza-Cope rearrangement of dienyltriazoles.

Authors:  Erica E Schultz; Vincent N G Lindsay; Richmond Sarpong
Journal:  Angew Chem Int Ed Engl       Date:  2014-07-15       Impact factor: 15.336

8.  Intramolecular transannulation of alkynyl triazoles via alkyne-carbene metathesis step: access to fused pyrroles.

Authors:  Yi Shi; Vladimir Gevorgyan
Journal:  Org Lett       Date:  2013-10-04       Impact factor: 6.005

9.  Stereoselective 1,3-insertions of rhodium(II) azavinyl carbenes.

Authors:  Stepan Chuprakov; Brady T Worrell; Nicklas Selander; Rakesh K Sit; Valery V Fokin
Journal:  J Am Chem Soc       Date:  2013-12-17       Impact factor: 15.419

10.  Transannulation of 1-sulfonyl-1,2,3-triazoles with heterocumulenes.

Authors:  Stepan Chuprakov; Sen Wai Kwok; Valery V Fokin
Journal:  J Am Chem Soc       Date:  2013-03-15       Impact factor: 15.419
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