Literature DB >> 28994229

General and Efficient Intermolecular [2+2] Photodimerization of Chalcones and Cinnamic Acid Derivatives in Solution through Visible-Light Catalysis.

Tao Lei1, Chao Zhou1, Mao-Yong Huang1, Lei-Min Zhao1, Bing Yang1, Chen Ye1, Hongyan Xiao1, Qing-Yuan Meng1, Vaidhyanathan Ramamurthy2, Chen-Ho Tung1, Li-Zhu Wu1.   

Abstract

[2+2] Photocycloaddition, for example, the dimerization of chalcones and cinnamic acid derivatives, is a unique strategy to construct cyclobutanes, which are building blocks for a variety of biologically active molecules and natural products. However, most attempts at the above [2+2] addition have focused on solid-state, molten-state, or host-guest systems under ultraviolet-light irradiation in order to overcome the competition of facile geometric isomerization of nonrigid olefins. We report a general and simple method to realize the intermolecular [2+2] dimerization reaction of these acyclic olefins to construct cyclobutanes in a highly regio- and diastereoselective manner in solution under visible light, which provides an efficient solution to a long-standing problem.
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  [2+2] cycloaddition; chalcones; cinnamic acid; cyclobutanes; visible-light catalysis

Year:  2017        PMID: 28994229     DOI: 10.1002/anie.201708559

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


  11 in total

1.  Crystal Engineering Construction of Caffeic Acid Derivatives with Potential Applications in Pharmaceuticals and Degradable Polymeric Materials.

Authors:  Zhihan Wang; Quinton Flores; Hongye Guo; Raquel Trevizo; Xiaochan Zhang; Shihan Wang
Journal:  CrystEngComm       Date:  2020-10-26       Impact factor: 3.545

2.  Enantioselective [2+2] Cycloadditions of Cinnamate Esters: Generalizing Lewis Acid Catalysis of Triplet Energy Transfer.

Authors:  Mary Elisabeth Daub; Hoimin Jung; Byung Joo Lee; Joonghee Won; Mu-Hyun Baik; Tehshik P Yoon
Journal:  J Am Chem Soc       Date:  2019-06-07       Impact factor: 15.419

3.  β-Selective Aroylation of Activated Alkenes by Photoredox Catalysis.

Authors:  Zhen Lei; Arghya Banerjee; Elena Kusevska; Eric Rizzo; Peng Liu; Ming-Yu Ngai
Journal:  Angew Chem Int Ed Engl       Date:  2019-04-17       Impact factor: 15.336

4.  Bromine Radical Catalysis by Energy Transfer Photosensitization.

Authors:  Dian-Feng Chen; Cameron H Chrisman; Garret M Miyake
Journal:  ACS Catal       Date:  2020-01-30       Impact factor: 13.084

5.  Synthesis of esters of diaminotruxillic bis-amino acids by Pd-mediated photocycloaddition of analogs of the Kaede protein chromophore.

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Journal:  Beilstein J Org Chem       Date:  2020-05-25       Impact factor: 2.883

6.  Effect of Reaction Media on Photosensitized [2+2]-Cycloaddition of Cinnamates.

Authors:  Alex Abramov; Oliver Reiser; David Díaz Díaz
Journal:  ChemistryOpen       Date:  2020-05-05       Impact factor: 2.911

7.  Chiral Brønsted acid-controlled intermolecular asymmetric [2 + 2] photocycloadditions.

Authors:  Evan M Sherbrook; Matthew J Genzink; Bohyun Park; Ilia A Guzei; Mu-Hyun Baik; Tehshik P Yoon
Journal:  Nat Commun       Date:  2021-09-30       Impact factor: 17.694

8.  Dimerizing cascades of enallenamides reveal the visible-light-promoted activation of cumulated C-C double bonds.

Authors:  Andrea Serafino; Maurizio Chiminelli; Davide Balestri; Luciano Marchiò; Franca Bigi; Rai-Mondo Maggi; Max Malacria; Giovanni Maestri
Journal:  Chem Sci       Date:  2022-01-26       Impact factor: 9.825

9.  Stereoselective, Ruthenium-Photocatalyzed Synthesis of 1,2-Diaminotruxinic Bis-amino Acids from 4-Arylidene-5(4H)-oxazolones.

Authors:  Sonia Sierra; M Victoria Gomez; Ana I Jiménez; Alexandra Pop; Cristian Silvestru; Maria Luisa Marín; Francisco Boscá; Germán Sastre; Enrique Gómez-Bengoa; Esteban P Urriolabeitia
Journal:  J Org Chem       Date:  2022-02-10       Impact factor: 4.354

10.  Cage-confined photocatalysis for wide-scope unusually selective [2 + 2] cycloaddition through visible-light triplet sensitization.

Authors:  Jing-Si Wang; Kai Wu; Changzhen Yin; Kang Li; Yahao Huang; Jia Ruan; Ximin Feng; Peng Hu; Cheng-Yong Su
Journal:  Nat Commun       Date:  2020-09-16       Impact factor: 14.919

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