Literature DB >> 30779561

Sulfamate Esters Guide C(3)-Selective Xanthylation of Alkanes.

Suraj K Ayer1, J L Roizen1.   

Abstract

Owing to the pervasiveness of hydroxyl groups in natural isolates, alcohol derivatives are alluring directing groups. Herein, an alcohol-derived sulfamate ester guides the light-initiated xanthylation of primary, secondary, or tertiary centers. This process enables formal directed deuteration, azidation, thiolation, and vinylation reactions.

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Year:  2019        PMID: 30779561      PMCID: PMC6656367          DOI: 10.1021/acs.joc.9b00105

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  58 in total

1.  Organometallic chemistry: C-H activation.

Authors:  Robert G Bergman
Journal:  Nature       Date:  2007-03-22       Impact factor: 49.962

2.  Deoxygenation of alcohols employing water as the hydrogen atom source.

Authors:  David A Spiegel; Kenneth B Wiberg; Laura N Schacherer; Matthew R Medeiros; John L Wood
Journal:  J Am Chem Soc       Date:  2005-09-14       Impact factor: 15.419

3.  A novel approach for the formation of carbon-nitrogen bonds: azidation of alkyl radicals with sulfonyl azides.

Authors:  C Ollivier; P Renaud
Journal:  J Am Chem Soc       Date:  2001-05-23       Impact factor: 15.419

4.  Intramolecular PhI=O mediated copper-catalyzed aziridination of unsaturated sulfamates: a new direct access to polysubstituted amines from simple homoallylic alcohols.

Authors:  Fernando Duran; Loïc Leman; Alberto Ghini; Gerardo Burton; Philippe Dauban; Robert H Dodd
Journal:  Org Lett       Date:  2002-07-25       Impact factor: 6.005

5.  EPR studies of amine radical cations, part 1: thermal and photoinduced rearrangements of n-alkylamine radical cations to their distonic forms in low-temperature freon matrices.

Authors:  I Janovský; W Knolle; S Naumov; F Williams
Journal:  Chemistry       Date:  2004-10-25       Impact factor: 5.236

6.  O-alkyl S-3,3-dimethyl-2-oxobutyl dithiocarbonates as versatile sulfur-transfer agents in radical C(sp3)-H functionalization.

Authors:  Akinori Sato; Hideki Yorimitsu; Koichiro Oshima
Journal:  Chem Asian J       Date:  2007-12-03

Review 7.  Catalytic C-H functionalization by metal carbenoid and nitrenoid insertion.

Authors:  Huw M L Davies; James R Manning
Journal:  Nature       Date:  2008-01-24       Impact factor: 49.962

8.  A predictably selective aliphatic C-H oxidation reaction for complex molecule synthesis.

Authors:  Mark S Chen; M Christina White
Journal:  Science       Date:  2007-11-02       Impact factor: 47.728

9.  Syntheses of the Stemona alkaloids (+/-)-stenine, (+/-)-neostenine, and (+/-)-13-epineostenine using a stereodivergent Diels-Alder/azido-Schmidt reaction.

Authors:  Kevin J Frankowski; Jennifer E Golden; Yibin Zeng; Yao Lei; Jeffrey Aubé
Journal:  J Am Chem Soc       Date:  2008-04-09       Impact factor: 15.419

10.  Cobalt-catalyzed intramolecular C-H amination with arylsulfonyl azides.

Authors:  Joshua V Ruppel; Rajesh M Kamble; X Peter Zhang
Journal:  Org Lett       Date:  2007-10-13       Impact factor: 6.005

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  7 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.  Copper-Catalyzed, N-Directed Csp3-H Trifluoromethylthiolation (-SCF3) and Trifluoromethylselenation (-SeCF3).

Authors:  Atanu Modak; Emily N Pinter; Silas P Cook
Journal:  J Am Chem Soc       Date:  2019-11-07       Impact factor: 15.419

3.  Photochemically-Mediated, Nickel-Catalyzed Synthesis of N-(Hetero)aryl Sulfamate Esters.

Authors:  J Miles Blackburn; Anastasia L Gant Kanegusuku; Georgia E Scott; Jennifer L Roizen
Journal:  Org Lett       Date:  2019-08-22       Impact factor: 6.005

Review 4.  Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis.

Authors:  Philip R D Murray; James H Cox; Nicholas D Chiappini; Casey B Roos; Elizabeth A McLoughlin; Benjamin G Hejna; Suong T Nguyen; Hunter H Ripberger; Jacob M Ganley; Elaine Tsui; Nick Y Shin; Brian Koronkiewicz; Guanqi Qiu; Robert R Knowles
Journal:  Chem Rev       Date:  2021-11-23       Impact factor: 60.622

Review 5.  Strategies to Generate Nitrogen-centered Radicals That May Rely on Photoredox Catalysis: Development in Reaction Methodology and Applications in Organic Synthesis.

Authors:  Kitae Kwon; R Thomas Simons; Meganathan Nandakumar; Jennifer L Roizen
Journal:  Chem Rev       Date:  2021-10-08       Impact factor: 60.622

Review 6.  Recent Advances in Photoredox-Mediated Radical Conjugate Addition Reactions: An Expanding Toolkit for the Giese Reaction.

Authors:  Anastasia L Gant Kanegusuku; Jennifer L Roizen
Journal:  Angew Chem Int Ed Engl       Date:  2021-07-21       Impact factor: 16.823

7.  Sulfamides direct radical-mediated chlorination of aliphatic C-H bonds.

Authors:  Melanie A Short; Mina F Shehata; Matthew A Sanders; Jennifer L Roizen
Journal:  Chem Sci       Date:  2019-11-08       Impact factor: 9.825

  7 in total

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