Literature DB >> 34750786

Photochemical C-H acetalization of O-heterocycles utilizing phenylglyoxylic acid as the photoinitiator.

Giorgos S Koutoulogenis1, Nikoleta Spiliopoulou1, Christoforos G Kokotos2.   

Abstract

A novel, mild, metal-free and easy-to-execute procedure for the C-H acetalization of O-heterocycles via visible light activation is presented, utilizing phenylglyoxylic acid as the photoinitiator. Biomass-derived O-heterocycles, like THF, can be employed, while primary, secondary alcohols and alcohols bearing a variety of functionalities were succesfully employed, affording the desired acetals in high yields. Facile acidic deprotection was also performed.
© 2021. The Author(s), under exclusive licence to European Photochemistry Association, European Society for Photobiology.

Entities:  

Keywords:  Phenylglyoxylic acid; Photochemical C–H acetalization; Photoinitiator; Photoorganocatalysis

Mesh:

Substances:

Year:  2021        PMID: 34750786     DOI: 10.1007/s43630-021-00126-7

Source DB:  PubMed          Journal:  Photochem Photobiol Sci        ISSN: 1474-905X            Impact factor:   4.328


  27 in total

Review 1.  Photocatalysis for the formation of the C-C bond.

Authors:  Maurizio Fagnoni; Daniele Dondi; Davide Ravelli; Angelo Albini
Journal:  Chem Rev       Date:  2007-05-27       Impact factor: 60.622

Review 2.  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

Review 3.  Applications of Continuous-Flow Photochemistry in Organic Synthesis, Material Science, and Water Treatment.

Authors:  Dario Cambié; Cecilia Bottecchia; Natan J W Straathof; Volker Hessel; Timothy Noël
Journal:  Chem Rev       Date:  2016-03-03       Impact factor: 60.622

4.  Decatungstate Anion for Photocatalyzed "Window Ledge" Reactions.

Authors:  Davide Ravelli; Stefano Protti; Maurizio Fagnoni
Journal:  Acc Chem Res       Date:  2016-09-20       Impact factor: 22.384

5.  A convenient synthesis of 2-tetrahydrofuranyl ethers.

Authors:  R Baati; A Valleix; C Mioskowski; D K Barma; J R Falck
Journal:  Org Lett       Date:  2000-02-24       Impact factor: 6.005

6.  Copper-catalyzed formation of C-O bonds by direct α-C-H bond activation of ethers using stoichiometric amounts of peroxide in batch and continuous-flow formats.

Authors:  G Sathish Kumar; Bartholomäus Pieber; K Rajender Reddy; C Oliver Kappe
Journal:  Chemistry       Date:  2012-04-11       Impact factor: 5.236

7.  Merging Visible Light Photoredox and Gold Catalysis.

Authors:  Matthew N Hopkinson; Adrian Tlahuext-Aca; Frank Glorius
Journal:  Acc Chem Res       Date:  2016-09-09       Impact factor: 22.384

8.  Chiral Diaryliodonium Phosphate Enables Light Driven Diastereoselective α-C(sp3)-H Acetalization.

Authors:  Baihua Ye; Jie Zhao; Ke Zhao; Jeffrey M McKenna; F Dean Toste
Journal:  J Am Chem Soc       Date:  2018-06-25       Impact factor: 15.419

Review 9.  Photochemical Approaches to Complex Chemotypes: Applications in Natural Product Synthesis.

Authors:  Markus D Kärkäs; John A Porco; Corey R J Stephenson
Journal:  Chem Rev       Date:  2016-04-27       Impact factor: 60.622

10.  Re2O7-catalyzed reaction of hemiacetals and aldehydes with O-, S-, and C-nucleophiles.

Authors:  Wantanee Sittiwong; Michael W Richardson; Charles E Schiaffo; Thomas J Fisher; Patrick H Dussault
Journal:  Beilstein J Org Chem       Date:  2013-07-30       Impact factor: 2.883

View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.