Literature DB >> 23646846

Pd-catalyzed Suzuki-Miyaura cross-coupling reactions between sulfamates and potassium Boc-protected aminomethyltrifluoroborates.

Gary A Molander1, Inji Shin.   

Abstract

Sulfamates were studied as the electrophilic partners in the palladium-catalyzed Suzuki-Miyaura cross-coupling reaction with potassium Boc-protected primary and secondary aminomethyltrifluoroborates. A broad range of substrates was successfully coupled to provide the desired products. Complex molecules containing a new carbon-carbon bond and an aminomethyl moiety could be prepared through this developed method.

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Year:  2013        PMID: 23646846      PMCID: PMC3796167          DOI: 10.1021/ol401021x

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


  21 in total

1.  Synthesis of amidomethyltrifluoroborates and their use in cross-coupling reactions.

Authors:  Gary A Molander; Marie-Aude Hiebel
Journal:  Org Lett       Date:  2010-11-05       Impact factor: 6.005

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

Authors:  Paul M Wehn; J Du Bois
Journal:  Org Lett       Date:  2005-10-13       Impact factor: 6.005

3.  Synthesis and Suzuki-Miyaura cross-coupling reactions of potassium Boc-protected aminomethyltrifluoroborate with aryl and hetaryl halides.

Authors:  Gary A Molander; Inji Shin
Journal:  Org Lett       Date:  2011-07-06       Impact factor: 6.005

4.  Ni(COD)2/PCy3 catalyzed cross-coupling of aryl and heteroaryl neopentylglycolboronates with aryl and heteroaryl mesylates and sulfamates in THF at room temperature.

Authors:  Pawaret Leowanawat; Na Zhang; Ana-Maria Resmerita; Brad M Rosen; Virgil Percec
Journal:  J Org Chem       Date:  2011-11-16       Impact factor: 4.354

5.  Potassium Boc-protected secondary aminomethyltrifluoroborates: synthesis and Suzuki-Miyaura cross-coupling reactions.

Authors:  Gary A Molander; Inji Shin
Journal:  Org Lett       Date:  2012-08-29       Impact factor: 6.005

6.  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

7.  Nickel-catalyzed C-O activation of phenol derivatives with potassium heteroaryltrifluoroborates.

Authors:  Gary A Molander; Floriane Beaumard
Journal:  Org Lett       Date:  2010-09-17       Impact factor: 6.005

8.  Suzuki-Miyaura coupling of aryl tosylates catalyzed by an array of indolyl phosphine-palladium catalysts.

Authors:  Chau Ming So; Chak Po Lau; Albert S C Chan; Fuk Yee Kwong
Journal:  J Org Chem       Date:  2008-09-11       Impact factor: 4.354

9.  Palladium-catalyzed Suzuki-Miyaura cross-couplings of aryl tosylates with potassium aryltrifluoroborates.

Authors:  Liang Zhang; Tianhao Meng; Jie Wu
Journal:  J Org Chem       Date:  2007-11-02       Impact factor: 4.354

10.  Aminomethylations via cross-coupling of potassium organotrifluoroborates with aryl bromides.

Authors:  Gary A Molander; Deidre L Sandrock
Journal:  Org Lett       Date:  2007-03-17       Impact factor: 6.005

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  6 in total

1.  Cross-Coupling and Related Reactions: Connecting Past Success to the Development of New Reactions for the Future.

Authors:  Louis-Charles Campeau; Nilay Hazari
Journal:  Organometallics       Date:  2018-11-27       Impact factor: 3.876

2.  Pd-Catalyzed Suzuki-Miyaura and Hiyama-Denmark Couplings of Aryl Sulfamates.

Authors:  Patrick R Melvin; Nilay Hazari; Megan Mohadjer Beromi; Hemali P Shah; Michael J Williams
Journal:  Org Lett       Date:  2016-11-03       Impact factor: 6.005

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

4.  α-Arylation/Heteroarylation of Chiral α-Aminomethyltrifluoroborates by Synergistic Iridium Photoredox/Nickel Cross-Coupling Catalysis.

Authors:  Mirna El Khatib; Ricardo Augusto Massarico Serafim; Gary A Molander
Journal:  Angew Chem Int Ed Engl       Date:  2015-11-23       Impact factor: 15.336

5.  Nickel-catalyzed Suzuki-Miyaura couplings in green solvents.

Authors:  Stephen D Ramgren; Liana Hie; Yuxuan Ye; Neil K Garg
Journal:  Org Lett       Date:  2013-07-23       Impact factor: 6.005

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

  6 in total

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