Literature DB >> 25853884

Visible-light-promoted remote C(sp(3))-H amidation and chlorination.

Qixue Qin1, Shouyun Yu1.   

Abstract

A visible-light-promoted C(sp(3))-H amidation and chlorination of N-chlorosulfonamides (NCSs) is reported. This remote C(sp(3))-H functionalization can be achieved in weak basic solution at room temperature with as little as 0.1 mol % of a photocatalyst. A variety of nitrogen-containing heterocycles (up to 94% yield) and chlorides (up to 93% yield) are prepared from NCSs. Late-stage C(sp(3))-H functionalization of complex and biologically important (-)-cis-myrtanylamine and (+)-dehydroabietylamine derivatives can also be achieved with excellent yields and regioselectivity.

Entities:  

Year:  2015        PMID: 25853884     DOI: 10.1021/acs.orglett.5b00582

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


  26 in total

1.  Modifying Positional Selectivity in C-H Functionalization Reactions with Nitrogen-Centered Radicals: Generalizable Approaches to 1,6-Hydrogen-Atom Transfer Processes.

Authors:  Melanie A Short; J Miles Blackburn; Jennifer L Roizen
Journal:  Synlett       Date:  2019-11-27       Impact factor: 2.454

2.  Merging Photochemistry with Electrochemistry: Functional-Group Tolerant Electrochemical Amination of C(sp3 )-H Bonds.

Authors:  Fei Wang; Shannon S Stahl
Journal:  Angew Chem Int Ed Engl       Date:  2019-03-14       Impact factor: 15.336

Review 3.  Complementary Strategies for Directed C(sp3 )-H Functionalization: A Comparison of Transition-Metal-Catalyzed Activation, Hydrogen Atom Transfer, and Carbene/Nitrene Transfer.

Authors:  John C K Chu; Tomislav Rovis
Journal:  Angew Chem Int Ed Engl       Date:  2017-12-05       Impact factor: 15.336

4.  Sulfamate Esters Guide Selective Radical-Mediated Chlorination of Aliphatic C-H Bonds.

Authors:  Melanie A Short; J Miles Blackburn; Jennifer L Roizen
Journal:  Angew Chem Int Ed Engl       Date:  2017-12-07       Impact factor: 15.336

5.  Metal-free Regioselective Hydrochlorination of Unactivated Alkenes via a Combined Acid Catalytic System.

Authors:  Shengzong Liang; Gerald B Hammond; Bo Xu
Journal:  Green Chem       Date:  2018-01-02       Impact factor: 10.182

6.  Remote C-H Functionalization via Selective Hydrogen Atom Transfer.

Authors:  Leah M Stateman; Kohki M Nakafuku; David A Nagib
Journal:  Synthesis (Stuttg)       Date:  2018-02-12       Impact factor: 3.157

7.  Synthesis of Alkyl Halides from Aldehydes via Deformylative Halogenation.

Authors:  Shengzong Liang; Tatsuya Kumon; Ricardo A Angnes; Melissa Sanchez; Bo Xu; Gerald B Hammond
Journal:  Org Lett       Date:  2019-05-03       Impact factor: 6.005

8.  Metal-Catalyzed and Metal-Free Intermolecular Amination of Light Alkanes and Benzenes.

Authors:  Pericles Stavropoulos
Journal:  Comments Mod Chem A Comments Inorg Chem       Date:  2016-04-29       Impact factor: 4.533

9.  Advances in Photocatalysis: A Microreview of Visible Light Mediated Ruthenium and Iridium Catalyzed Organic Transformations.

Authors:  Jon I Day; Kip Teegardin; Jimmie Weaver; John Chan
Journal:  Org Process Res Dev       Date:  2016-06-28       Impact factor: 3.317

10.  A General Approach to Site-Specific, Intramolecular C-H Functionalization Using Dithiocarbamates.

Authors:  Christina G Na; Erik J Alexanian
Journal:  Angew Chem Int Ed Engl       Date:  2018-09-03       Impact factor: 15.336

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