Literature DB >> 29048913

Synthesis of N-Substituted Sulfamate Esters from Sulfamic Acid Salts by Activation with Triphenylphosphine Ditriflate.

J Miles Blackburn1, Melanie A Short1, Thomas Castanheiro1, Suraj K Ayer1, Tobias D Muellers1, Jennifer L Roizen1.   

Abstract

A general approach to access sulfamate esters through preparation of sulfamic acid salts, subsequent activation with triphenylphosphine ditriflate, and nucleophilic trapping is disclosed. The method proceeds in modest to excellent yields to incorporate nucleophiles derived from aliphatic alcohols and phenols. This approach can be employed to furnish differentially substituted sulfamides.

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Year:  2017        PMID： 29048913      PMCID： PMC5716482          DOI： 10.1021/acs.orglett.7b03059

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


  18 in total

1.  Introduction of 2,2,2-trichloroethyl-protected sulfates into monosaccharides with a sulfuryl imidazolium salt and application to the synthesis of sulfated carbohydrates.

Authors:  Laura J Ingram; Scott D Taylor
Journal:  Angew Chem Int Ed Engl       Date:  2006-05-19       Impact factor: 15.336

2.  Enantioselective C-H amination using cationic ruthenium(II)-pybox catalysts.

Authors:  Erika Milczek; Nadège Boudet; Simon Blakey
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

3.  Iron-catalyzed coupling of aryl sulfamates and aryl/vinyl tosylates with aryl Grignards.

Authors:  Toolika Agrawal; Silas P Cook
Journal:  Org Lett       Date:  2014-09-17       Impact factor: 6.005

4.  Room Temperature Activation of Aryloxysulfonyl Azides by [Co(II)(TPP)] for Selective Radical Aziridination of Alkenes via Metalloradical Catalysis.

Authors:  Velusamy Subbarayan; Li-Mei Jin; Cui Xin; X Peter Zhang
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

5.  Suzuki-Miyaura cross-coupling of aryl carbamates and sulfamates: experimental and computational studies.

Authors:  Kyle W Quasdorf; Aurora Antoft-Finch; Peng Liu; Amanda L Silberstein; Anna Komaromi; Tom Blackburn; Stephen D Ramgren; K N Houk; Victor Snieckus; Neil K Garg
Journal:  J Am Chem Soc       Date:  2011-04-01       Impact factor: 15.419

6.  Synthesis and comparative molecular field analysis (CoMFA) of symmetric and nonsymmetric cyclic sulfamide HIV-1 protease inhibitors.

Authors:  W Schaal; A Karlsson; G Ahlsén; J Lindberg; H O Andersson; U H Danielson; B Classon; T Unge; B Samuelsson; J Hultén; A Hallberg; A Karlén
Journal:  J Med Chem       Date:  2001-01-18       Impact factor: 7.446

7.  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

Review 8.  Sulfamates and their therapeutic potential.

Authors:  Jean-Yves Winum; Andrea Scozzafava; Jean-Louis Montero; Claudiu T Supuran
Journal:  Med Res Rev       Date:  2005-03       Impact factor: 12.944

9.  Direct synthesis of sulfonamides and activated sulfonate esters from sulfonic acids.

Authors:  Stephen Caddick; Jonathan D Wilden; Duncan B Judd
Journal:  J Am Chem Soc       Date:  2004-02-04       Impact factor: 15.419

10.  Nonheme iron-mediated amination of C(sp3)-H bonds. Quinquepyridine-supported iron-imide/nitrene intermediates by experimental studies and DFT calculations.

Authors:  Yungen Liu; Xiangguo Guan; Ella Lai-Ming Wong; Peng Liu; Jie-Sheng Huang; Chi-Ming Che
Journal:  J Am Chem Soc       Date:  2013-05-02       Impact factor: 15.419
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  8 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.  Sulfamate Esters Guide C(3)-Selective Xanthylation of Alkanes.

Authors:  Suraj K Ayer; J L Roizen
Journal:  J Org Chem       Date:  2019-02-26       Impact factor: 4.354

3.  Photochemically Mediated Nickel-Catalyzed Synthesis of N-(Hetero)aryl Sulfamides.

Authors:  R Thomas Simons; Georgia E Scott; Anastasia Gant Kanegusuku; Jennifer L Roizen
Journal:  J Org Chem       Date:  2020-05-04       Impact factor: 4.354

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.  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 6.  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 7.  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

8.  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
  8 in total

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