Literature DB >> 26228259

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

Jiang Wang1, Nan Zheng2.   

Abstract

We report the first example of an intermolecular [4+2] annulation of cyclobutylanilines with alkynes enabled by visible-light photocatalysis. Monocyclic and bicyclic cyclobutylanilines successfully undergo the annulation with terminal and internal alkynes to generate a wide variety of amine-substituted cyclohexenes including new hydrindan and decalin derivatives with good to excellent diastereoselectivity. The reaction is overall redox neutral with perfect atom economy.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  N-aryl cyclobutyl amines; cyclohexenes; iridium catalyst; photocatalysis; small ring systems

Mesh：

Substances：

Year:  2015        PMID： 26228259      PMCID： PMC4653064          DOI： 10.1002/anie.201504076

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


  34 in total

Review 1.  Heterocycles from cyclopropanes: applications in natural product synthesis.

Authors:  Cheryl A Carson; Michael A Kerr
Journal:  Chem Soc Rev       Date:  2009-07-10       Impact factor: 54.564

2.  The formal [4+3] cycloaddition between donor-acceptor cyclobutanes and nitrones.

Authors:  Andrew C Stevens; Cory Palmer; Brian L Pagenkopf
Journal:  Org Lett       Date:  2011-02-22       Impact factor: 6.005

3.  Regioselective inter- and intramolecular formal [4+2] cycloaddition of cyclobutanones with indoles and total synthesis of (±)-aspidospermidine.

Authors:  Mizuki Kawano; Takaaki Kiuchi; Shoko Negishi; Hiroyuki Tanaka; Takaya Hoshikawa; Jun-ichi Matsuo; Hiroyuki Ishibashi
Journal:  Angew Chem Int Ed Engl       Date:  2012-11-26       Impact factor: 15.336

Review 4.  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

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

Authors:  Theresa H Nguyen; Scott A Morris; Nan Zheng
Journal:  Adv Synth Catal       Date:  2014-09-15       Impact factor: 5.837

6.  Cyclobutanes in catalysis.

Authors:  Tobias Seiser; Tanguy Saget; Duc N Tran; Nicolai Cramer
Journal:  Angew Chem Int Ed Engl       Date:  2011-07-26       Impact factor: 15.336

7.  Single-electron transmetalation: an enabling technology for secondary alkylboron cross-coupling.

Authors:  David N Primer; Idris Karakaya; John C Tellis; Gary A Molander
Journal:  J Am Chem Soc       Date:  2015-02-04       Impact factor: 15.419

8.  Ring-strain-enabled reaction discovery: new heterocycles from bicyclo[1.1.0]butanes.

Authors:  Maciej A A Walczak; Tanja Krainz; Peter Wipf
Journal:  Acc Chem Res       Date:  2015-03-16       Impact factor: 22.384

9.  Evolution of a fourth generation catalyst for the amination and thioetherification of aryl halides.

Authors:  John F Hartwig
Journal:  Acc Chem Res       Date:  2008-11-18       Impact factor: 22.384

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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  4 in total

1.  Visible-Light-Mediated [4+2] Annulation of N-Cyclobutylanilines with Alkynes Catalyzed by Self-Doped Ti3+ @TiO2.

Authors:  Jiang Wang; Chengyu Mao; Pingyun Feng; Nan Zheng
Journal:  Chemistry       Date:  2017-08-09       Impact factor: 5.236

2.  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

3.  Advances in Photocatalysis: A Microreview of Visible Light Mediated Ruthenium and Iridium Catalyzed Organic Transformations.

Authors:  Jon I Day; Kip Teegardin; Jimmie Weaver; John Chan
Journal:  Org Process Res Dev       Date:  2016-06-28       Impact factor: 3.317

4.  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
  4 in total

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