Literature DB >> 16209510

Exploring new uses for C-H amination: Ni-catalyzed cross-coupling of cyclic sulfamates.

Paul M Wehn1, J Du Bois.   

Abstract

[reaction: see text] Benzene-fused cyclic sulfamates are prepared from ortho-substituted phenolic starting materials through selective C-H amination or olefin aziridination. These unique heterocycles will engage in Ni-catalyzed cross-coupling reactions with aryl- and alkyl-Grignard reagents. Application of modern tools for C-N and C-C bond formation thus makes readily available functional amine derivatives and augments the possible uses for C-H amination in synthesis.

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Year:  2005        PMID: 16209510     DOI: 10.1021/ol051896l

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


  14 in total

Review 1.  Nickel-catalyzed cross-couplings involving carbon-oxygen bonds.

Authors:  Brad M Rosen; Kyle W Quasdorf; Daniella A Wilson; Na Zhang; Ana-Maria Resmerita; Neil K Garg; Virgil Percec
Journal:  Chem Rev       Date:  2010-12-06       Impact factor: 60.622

2.  A stereoselective synthesis of the bromopyrrole natural product (-)-agelastatin A.

Authors:  Paul M Wehn; J Du Bois
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

Review 3.  Advances in transition metal (Pd, Ni, Fe)-catalyzed cross-coupling reactions using alkyl-organometallics as reaction partners.

Authors:  Ranjan Jana; Tejas P Pathak; Matthew S Sigman
Journal:  Chem Rev       Date:  2011-02-14       Impact factor: 60.622

4.  Heterocycles via intramolecular platinum-catalyzed propargylic substitution.

Authors:  Qiren Liang; Jef K De Brabander
Journal:  Tetrahedron       Date:  2011-07-08       Impact factor: 2.457

5.  Nickel-catalyzed amination of aryl sulfamates.

Authors:  Stephen D Ramgren; Amanda L Silberstein; Yang Yang; Neil K Garg
Journal:  Angew Chem Int Ed Engl       Date:  2011-01-20       Impact factor: 15.336

6.  Mechanism and Origins of Ligand-Controlled Stereoselectivity of Ni-Catalyzed Suzuki-Miyaura Coupling with Benzylic Esters: A Computational Study.

Authors:  Shuo-Qing Zhang; Buck L H Taylor; Chong-Lei Ji; Yuan Gao; Michael R Harris; Luke E Hanna; Elizabeth R Jarvo; K N Houk; Xin Hong
Journal:  J Am Chem Soc       Date:  2017-09-07       Impact factor: 15.419

7.  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

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

Authors:  J Miles Blackburn; Melanie A Short; Thomas Castanheiro; Suraj K Ayer; Tobias D Muellers; Jennifer L Roizen
Journal:  Org Lett       Date:  2017-11-03       Impact factor: 6.005

9.  Nickel-catalyzed amination of aryl sulfamates and carbamates using an air-stable precatalyst.

Authors:  Liana Hie; Stephen D Ramgren; Tehetena Mesganaw; Neil K Garg
Journal:  Org Lett       Date:  2012-07-31       Impact factor: 6.005

10.  Suzuki-Miyaura coupling of aryl carbamates, carbonates, and sulfamates.

Authors:  Kyle W Quasdorf; Michelle Riener; Krastina V Petrova; Neil K Garg
Journal:  J Am Chem Soc       Date:  2009-12-16       Impact factor: 15.419

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