Literature DB >> 26322524

Oxalates as Activating Groups for Alcohols in Visible Light Photoredox Catalysis: Formation of Quaternary Centers by Redox-Neutral Fragment Coupling.

Christopher C Nawrat1, Christopher R Jamison2, Yuriy Slutskyy2, David W C MacMillan1, Larry E Overman2.   

Abstract

Alkyl oxalates are new bench-stable alcohol-activating groups for radical generation under visible light photoredox conditions. Using these precursors, the first net redox-neutral coupling of tertiary and secondary alcohols with electron-deficient alkenes is achieved.

Entities:  

Mesh：

Substances：

Year:  2015        PMID： 26322524      PMCID： PMC4632490          DOI： 10.1021/jacs.5b07678

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  12 in total

1.  Deoxygenative functionalization of hydroxy groups via xanthates with tetraphenyldisilane

Authors: 
Journal:  J Org Chem       Date:  2000-05-09       Impact factor: 4.354

2.  Enantioselective radical processes.

Authors:  Mukund P Sibi; Shankar Manyem; Jake Zimmerman
Journal:  Chem Rev       Date:  2003-08       Impact factor: 60.622

3.  Shining light on photoredox catalysis: theory and synthetic applications.

Authors:  Joseph W Tucker; Corey R J Stephenson
Journal:  J Org Chem       Date:  2012-01-26       Impact factor: 4.354

4.  Constructing quaternary stereogenic centers using tertiary organocuprates and tertiary radicals. Total synthesis of trans-clerodane natural products.

Authors:  Daniel S Müller; Nicholas L Untiedt; André P Dieskau; Gregory L Lackner; Larry E Overman
Journal:  J Am Chem Soc       Date:  2015-01-13       Impact factor: 15.419

5.  Fragment Coupling and the Construction of Quaternary Carbons Using Tertiary Radicals Generated From tert-Alkyl N-Phthalimidoyl Oxalates By Visible-Light Photocatalysis.

Authors:  Gregory L Lackner; Kyle W Quasdorf; Gerald Pratsch; Larry E Overman
Journal:  J Org Chem       Date:  2015-06-01       Impact factor: 4.354

Review 6.  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

7.  Direct construction of quaternary carbons from tertiary alcohols via photoredox-catalyzed fragmentation of tert-alkyl N-phthalimidoyl oxalates.

Authors:  Gregory L Lackner; Kyle W Quasdorf; Larry E Overman
Journal:  J Am Chem Soc       Date:  2013-10-02       Impact factor: 15.419

Review 8.  Solar synthesis: prospects in visible light photocatalysis.

Authors:  Danielle M Schultz; Tehshik P Yoon
Journal:  Science       Date:  2014-02-28       Impact factor: 47.728

9.  A practical and catalytic reductive olefin coupling.

Authors:  Julian C Lo; Yuki Yabe; Phil S Baran
Journal:  J Am Chem Soc       Date:  2014-01-15       Impact factor: 15.419

10.  Carboxylic acids as a traceless activation group for conjugate additions: a three-step synthesis of (±)-pregabalin.

Authors:  Lingling Chu; Chisa Ohta; Zhiwei Zuo; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2014-07-28       Impact factor: 15.419
View more
  39 in total

1.  Forging C(sp3)-C(sp3) Bonds with Carbon-Centered Radicals in the Synthesis of Complex Molecules.

Authors:  Spencer P Pitre; Nicholas A Weires; Larry E Overman
Journal:  J Am Chem Soc       Date:  2019-01-04       Impact factor: 15.419

2.  Enantioselective Construction of Acyclic Quaternary Carbon Stereocenters: Palladium-Catalyzed Decarboxylative Allylic Alkylation of Fully Substituted Amide Enolates.

Authors:  Pavel Starkov; Jared T Moore; Douglas C Duquette; Brian M Stoltz; Ilan Marek
Journal:  J Am Chem Soc       Date:  2017-07-07       Impact factor: 15.419

3.  Photochemical Perfluoroalkylation with Pyridine N-Oxides: Mechanistic Insights and Performance on a Kilogram Scale.

Authors:  Joel W Beatty; James J Douglas; Richard Miller; Rory C McAtee; Kevin P Cole; Corey R J Stephenson
Journal:  Chem       Date:  2016-09-08       Impact factor: 22.804

4.  Facile Preparation of Spirolactones by an Alkoxycarbonyl Radical Cyclization-Cross-Coupling Cascade.

Authors:  Nicholas A Weires; Yuriy Slutskyy; Larry E Overman
Journal:  Angew Chem Int Ed Engl       Date:  2019-05-13       Impact factor: 15.336

5.  Harnessing Alkyl Amines as Electrophiles for Nickel-Catalyzed Cross Couplings via C-N Bond Activation.

Authors:  Corey H Basch; Jennie Liao; Jianyu Xu; Jacob J Piane; Mary P Watson
Journal:  J Am Chem Soc       Date:  2017-04-05       Impact factor: 15.419

6.  Transforming Olefins into γ,δ-Unsaturated Nitriles through Copper Catalysis.

Authors:  Xuesong Wu; Jan Riedel; Vy M Dong
Journal:  Angew Chem Int Ed Engl       Date:  2017-08-10       Impact factor: 15.336

7.  A Concise Approach to Paxilline Indole Diterpenes.

Authors:  David T George; Eric J Kuenstner; Sergey V Pronin
Journal:  J Am Chem Soc       Date:  2015-12-07       Impact factor: 15.419

8.  Generation of the Methoxycarbonyl Radical by Visible-Light Photoredox Catalysis and Its Conjugate Addition with Electron-Deficient Olefins.

Authors:  Yuriy Slutskyy; Larry E Overman
Journal:  Org Lett       Date:  2016-05-17       Impact factor: 6.005

9.  Tandem Rh-catalysis: decarboxylative β-keto acid and alkyne cross-coupling.

Authors:  Faben A Cruz; Zhiwei Chen; Sarah I Kurtoic; Vy M Dong
Journal:  Chem Commun (Camb)       Date:  2016-04-04       Impact factor: 6.222

10.  Ti-Catalyzed Radical Alkylation of Secondary and Tertiary Alkyl Chlorides Using Michael Acceptors.

Authors:  Xiangyu Wu; Wei Hao; Ke-Yin Ye; Binyang Jiang; Gisselle Pombar; Zhidong Song; Song Lin
Journal:  J Am Chem Soc       Date:  2018-10-26       Impact factor: 15.419
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.