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Literature DB >> 22129424

Synthesis of α-amino ketones from terminal alkynes via rhodium-catalyzed denitrogenative hydration of N-sulfonyl-1,2,3-triazoles.

Tomoya Miura¹, Tsuneaki Biyajima, Tetsuji Fujii, Masahiro Murakami.

Abstract

N-Sulfonyl-1,2,3-triazoles react with water in the presence of a rhodium catalyst to produce α-amino ketones in high yield. An intermediary α-imino rhodium(II) carbenoid undergoes insertion into the O-H bond of water. This transformation formally achieves 1,2-aminohydroxylation of terminal alkynes in a regioselective fashion when combined with the copper(I)-catalyzed 1,3-dipolar cycloaddition with N-sulfonyl azides.

Entities: Chemical

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Year: 2011 PMID： 22129424 DOI： 10.1021/ja2104203

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

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Cited

16 in total

1. Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines.

Authors: John M Bennett; Jonathan D Shapiro; Krystina N Choinski; Yingbin Mei; Sky M Aulita; Giovanny M Dominguez; Max M Majireck
Journal: J Vis Exp Date: 2018-01-03 Impact factor: 1.355

2. 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

3. 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

4. Catalytic asymmetric transannulation of NH-1,2,3-triazoles with olefins.

Authors: Sen Wai Kwok; Li Zhang; Neil P Grimster; Valery V Fokin
Journal: Angew Chem Int Ed Engl Date: 2014-03-24 Impact factor: 15.336

5. 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

6. 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

Synthesis of α-amino ketones from terminal alkynes via rhodium-catalyzed denitrogenative hydration of N-sulfonyl-1,2,3-triazoles.

1. Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines.

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

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

4. Catalytic asymmetric transannulation of NH-1,2,3-triazoles with olefins.

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

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

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

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

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

10. Arylation of rhodium(II) azavinyl carbenes with boronic acids.