Literature DB >> 26212794

Controllable Chemoselectivity in Visible-Light Photoredox Catalysis: Four Diverse Aerobic Radical Cascade Reactions.

Xinfei Liu1, Xinyi Ye2, Filip Bureš3, Hongjun Liu1, Zhiyong Jiang4.   

Abstract

Reported is the controllable selectivity syntheses of four distinct products from the same starting materials by visible-light photoredox catalysis. By employing a dicyanopyrazine-derived chromophore (DPZ) as photoredox catalyst, an aerobic radical mechanism has been developed, and allows the reactions of N-tetrahydroisoquinolines (THIQs) with N-itaconimides to through four different pathways, including addition-cyclization, addition-elimination, addition-coupling, and addition-protonation, with satisfactory chemoselectivity. The current strategy provide straightforward access to four different but valuable N-heterocyclic adducts in moderate to excellent yields.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  heterocycles; photochemisty; radicals; reaction mechanisms; synthetic methods

Mesh:

Substances:

Year:  2015        PMID: 26212794     DOI: 10.1002/anie.201505193

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


  7 in total

1.  Photoinitiated Cascade for Rapid Access to Pyrroloquinazolinone Core of Vasicinone, Luotonins, and Related Alkaloids.

Authors:  D Sai Reddy; Andrei G Kutateladze
Journal:  Org Lett       Date:  2019-04-01       Impact factor: 6.005

2.  Structural elaboration of dicyanopyrazine: towards push-pull molecules with tailored photoredox activity.

Authors:  Zuzana Hloušková; Milan Klikar; Oldřich Pytela; Numan Almonasy; Aleš Růžička; Veronika Jandová; Filip Bureš
Journal:  RSC Adv       Date:  2019-07-31       Impact factor: 4.036

Review 3.  Photoredox-Catalyzed C-H Functionalization Reactions.

Authors:  Natalie Holmberg-Douglas; David A Nicewicz
Journal:  Chem Rev       Date:  2021-09-29       Impact factor: 60.622

4.  Ground-State Electron Transfer as an Initiation Mechanism for Biocatalytic C-C Bond Forming Reactions.

Authors:  Haigen Fu; Heather Lam; Megan A Emmanuel; Ji Hye Kim; Braddock A Sandoval; Todd K Hyster
Journal:  J Am Chem Soc       Date:  2021-06-11       Impact factor: 16.383

5.  Highly chemo-, enantio-, and diastereoselective [4 + 2] cycloaddition of 5H-thiazol-4-ones with N-itaconimides.

Authors:  Shuai Qiu; Choon-Hong Tan; Zhiyong Jiang
Journal:  Beilstein J Org Chem       Date:  2016-11-01       Impact factor: 2.883

6.  Multifunctional Oxazolone Derivative as an Optical Amplifier, Generator, and Modulator.

Authors:  Adam Szukalski; Przemysław Krawczyk; Bouchta Sahraoui; Beata Jędrzejewska
Journal:  J Phys Chem B       Date:  2022-02-18       Impact factor: 2.991

7.  Radical-based functionalization-oriented construction: rapid assembly of azaarene-substituted highly functionalized pyrroles.

Authors:  Weigao Hu; Qiangqiang Zhan; Hongwei Zhou; Shanshan Cao; Zhiyong Jiang
Journal:  Chem Sci       Date:  2021-03-29       Impact factor: 9.825

  7 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.