Literature DB >> 26120292

Intermolecular [3+2] Annulation of Cyclopropylanilines with Alkynes, Enynes, and Diynes via Visible Light Photocatalysis.

Theresa H Nguyen1, Scott A Morris1, Nan Zheng1.   

Abstract

One-step synthesis of carbocycles substituted with amines from simple starting materials remains rare. We recently developed intermolecular [3+2] annulation of cyclopropylanilines with alkenes and alkynes that enable this one-step synthesis. Herein, we report our findings for a fullscale study of the annulation. Significant expansion of the substrate scope for both cyclopropylanilines and alkynes is achieved. A range of structurally diverse carbocycles substituted with amines is prepared.

Entities:  

Keywords:  [3+2] annulation; alkynes; cyclopropylanilines; diynes; enynes; intermolecular; photocatalysis; visible light

Year:  2014        PMID: 26120292      PMCID: PMC4478291          DOI: 10.1002/adsc.201400742

Source DB:  PubMed          Journal:  Adv Synth Catal        ISSN: 1615-4150            Impact factor:   5.837


  15 in total

1.  Cationic ruthenium(II) catalysts for oxidative C-H/N-H bond functionalizations of anilines with removable directing group: synthesis of indoles in water.

Authors:  Lutz Ackermann; Alexander V Lygin
Journal:  Org Lett       Date:  2012-01-13       Impact factor: 6.005

Review 2.  Diversity-oriented synthesis: producing chemical tools for dissecting biology.

Authors:  Cornelius J O' Connor; Henning S G Beckmann; David R Spring
Journal:  Chem Soc Rev       Date:  2012-04-10       Impact factor: 54.564

3.  Efficient N-p-methoxyphenyl amine deprotection through anodic oxidation.

Authors:  Sandra De Lamo Marin; Thierry Martens; Charles Mioskowski; Jacques Royer
Journal:  J Org Chem       Date:  2005-12-09       Impact factor: 4.354

4.  Ruthenium-catalyzed direct C-H bond arylations of heteroarenes.

Authors:  Lutz Ackermann; Alexander V Lygin
Journal:  Org Lett       Date:  2011-06-06       Impact factor: 6.005

5.  Ruthenium(0)-catalyzed sp3 C-H bond arylation of benzylic amines using arylboronates.

Authors:  Navid Dastbaravardeh; Michael Schnürch; Marko D Mihovilovic
Journal:  Org Lett       Date:  2012-03-26       Impact factor: 6.005

Review 6.  Visible light photoredox catalysis with transition metal complexes: applications in organic synthesis.

Authors:  Christopher K Prier; Danica A Rankic; David W C MacMillan
Journal:  Chem Rev       Date:  2013-03-19       Impact factor: 60.622

7.  Catalytic intermolecular β-C-H alkenylation of α-enamino-ketones with simple alkynes.

Authors:  Zhiqian Wang; Brandon J Reinus; Guangbin Dong
Journal:  Chem Commun (Camb)       Date:  2013-11-26       Impact factor: 6.222

8.  The first calibration of an aminiumyl radical ion clock: why N-cyclopropylanilines may be poor mechanistic probes for single electron transfer.

Authors:  Xiangzhong Li; Michelle L Grimm; Kazuo Igarashi; Neal Castagnoli; J M Tanko
Journal:  Chem Commun (Camb)       Date:  2007-04-03       Impact factor: 6.222

9.  Tunable cross coupling of silanols: selective synthesis of heavily substituted allenes and butadienes.

Authors:  Hui Zhou; Christina Moberg
Journal:  J Am Chem Soc       Date:  2012-09-18       Impact factor: 15.419

10.  Visible light mediated intermolecular [3 + 2] annulation of cyclopropylanilines with alkynes.

Authors:  Theresa H Nguyen; Soumitra Maity; Nan Zheng
Journal:  Beilstein J Org Chem       Date:  2014-04-29       Impact factor: 2.883

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  7 in total

1.  Detection of Fleeting Amine Radical Cations and Elucidation of Chain Processes in Visible-Light-Mediated [3 + 2] Annulation by Online Mass Spectrometric Techniques.

Authors:  Yi Cai; Jiang Wang; Yuexiang Zhang; Zhi Li; David Hu; Nan Zheng; Hao Chen
Journal:  J Am Chem Soc       Date:  2017-08-25       Impact factor: 15.419

2.  A general protocol for radical anion [3 + 2] cycloaddition enabled by tandem Lewis acid photoredox catalysis.

Authors:  Adrian G Amador; Evan M Sherbrook; Zhan Lu; Tehshik P Yoon
Journal:  Synthesis (Stuttg)       Date:  2017-10-19       Impact factor: 3.157

3.  Photochemical Formal (4 + 2)-Cycloaddition of Imine-Substituted Bicyclo[1.1.1]pentanes and Alkenes.

Authors:  Alexander S Harmata; Taylor E Spiller; Madison J Sowden; Corey R J Stephenson
Journal:  J Am Chem Soc       Date:  2021-12-13       Impact factor: 16.383

4.  The Cleavage of a C-C Bond in Cyclobutylanilines by Visible-Light Photoredox Catalysis: Development of a [4+2] Annulation Method.

Authors:  Jiang Wang; Nan Zheng
Journal:  Angew Chem Int Ed Engl       Date:  2015-07-24       Impact factor: 15.336

5.  Photoredox-catalyzed oxo-amination of aryl cyclopropanes.

Authors:  Liang Ge; Ding-Xing Wang; Renyi Xing; Di Ma; Patrick J Walsh; Chao Feng
Journal:  Nat Commun       Date:  2019-09-25       Impact factor: 14.919

6.  Photoinduced Remote Functionalisations by Iminyl Radical Promoted C-C and C-H Bond Cleavage Cascades.

Authors:  Elizabeth M Dauncey; Sara P Morcillo; James J Douglas; Nadeem S Sheikh; Daniele Leonori
Journal:  Angew Chem Int Ed Engl       Date:  2017-12-04       Impact factor: 15.336

7.  Synthesis of bicyclo[3.1.0]hexanes by (3 + 2) annulation of cyclopropenes with aminocyclopropanes.

Authors:  Bastian Muriel; Alec Gagnebin; Jerome Waser
Journal:  Chem Sci       Date:  2019-10-08       Impact factor: 9.825

  7 in total

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