Literature DB >> 19810764

Highly efficient oxidation of amines to imines by singlet oxygen and its application in Ugi-type reactions.

Gaoxi Jiang1, Jian Chen, Jie-Sheng Huang, Chi-Ming Che.   

Abstract

A variety of secondary benzylic amines were oxidized to imines in 90% to >99% yields by singlet oxygen generated from oxygen and a porphyrin photosensitizer. On the basis of these reactions, a protocol was developed for oxidative Ugi-type reactions with singlet oxygen as the oxidant. This protocol has been used to synthesize C1- and N-functionalized benzylic amines in up to 96% yields.

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Year:  2009        PMID: 19810764     DOI: 10.1021/ol9018166

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


  15 in total

Review 1.  Comprehensive survey of chemical libraries for drug discovery and chemical biology: 2009.

Authors:  Roland E Dolle; Bertrand Le Bourdonnec; Karin Worm; Guillermo A Morales; Craig J Thomas; Wei Zhang
Journal:  J Comb Chem       Date:  2010-10-05

Review 2.  Oxygen and ROS in Photosynthesis.

Authors:  Sergey Khorobrykh; Vesa Havurinne; Heta Mattila; Esa Tyystjärvi
Journal:  Plants (Basel)       Date:  2020-01-10

3.  An Ugi Reaction Incorporating a Redox-Neutral Amine C-H Functionalization Step.

Authors:  Zhengbo Zhu; Daniel Seidel
Journal:  Org Lett       Date:  2016-01-19       Impact factor: 6.005

4.  Efficient singlet oxygen generation by luminescent 2-(2′-thienyl)pyridyl cyclometalated platinum(II) complexes and their calixarene derivatives.

Authors:  Siu-Wai Lai; Ying Liu; Dong Zhang; Bin Wang; Chun-Nam Lok; Chi-Ming Che; Matthias Selke
Journal:  Photochem Photobiol       Date:  2010 Nov-Dec       Impact factor: 3.421

5.  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

6.  Evaluation of the catalytic activity and cytotoxicity of palladium nanocubes: the role of oxygen.

Authors:  Eshan Dahal; Jessica Curtiss; Deepak Subedi; Gen Chen; Jessica P Houston; Sergei Smirnov
Journal:  ACS Appl Mater Interfaces       Date:  2015-04-30       Impact factor: 9.229

7.  Active repair of a dinuclear photocatalyst for visible-light-driven hydrogen production.

Authors:  Michael G Pfeffer; Carolin Müller; Evelyn T E Kastl; Alexander K Mengele; Benedikt Bagemihl; Sven S Fauth; Johannes Habermehl; Lydia Petermann; Maria Wächtler; Martin Schulz; Daniel Chartrand; François Laverdière; Phillip Seeber; Stephan Kupfer; Stefanie Gräfe; Garry S Hanan; Johannes G Vos; Benjamin Dietzek-Ivanšić; Sven Rau
Journal:  Nat Chem       Date:  2022-02-07       Impact factor: 24.274

8.  A visible-light-mediated oxidative C-N bond formation/aromatization cascade: photocatalytic preparation of N-arylindoles.

Authors:  Soumitra Maity; Nan Zheng
Journal:  Angew Chem Int Ed Engl       Date:  2012-08-22       Impact factor: 15.336

Review 9.  Singlet oxygen generation by cyclometalated complexes and applications.

Authors:  David Ashen-Garry; Matthias Selke
Journal:  Photochem Photobiol       Date:  2013-12-18       Impact factor: 3.421

10.  Quinone-catalyzed oxidative deformylation: synthesis of imines from amino alcohols.

Authors:  Xinyun Liu; Johnny H Phan; Benjamin J Haugeberg; Shrikant S Londhe; Michael D Clift
Journal:  Beilstein J Org Chem       Date:  2017-12-28       Impact factor: 2.883

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