Literature DB >> 21732595

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

Gary A Molander1, Inji Shin.   

Abstract

Potassium Boc-protected aminomethyltrifluoroborate, a primary aminomethyl equivalent, was synthesized successfully through a "one-pot" process. With this trifluoroborate, Suzuki-Miyaura cross-coupling reactions were investigated with a variety of both aryl and hetaryl chlorides in good to excellent yields.
© 2011 American Chemical Society

Entities:  

Mesh:

Substances:

Year:  2011        PMID: 21732595      PMCID: PMC3146588          DOI: 10.1021/ol2014768

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


  13 in total

1.  Synthesis and SAR of novel isoquinoline CXCR4 antagonists with potent anti-HIV activity.

Authors:  John F Miller; Kristjan S Gudmundsson; Leah D'Aurora Richardson; Stephen Jenkinson; Andrew Spaltenstein; Michael Thomson; Pat Wheelan
Journal:  Bioorg Med Chem Lett       Date:  2010-05-15       Impact factor: 2.823

2.  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

3.  Reduction of organic compounds by lithium aluminum hydride; halides, quinones, miscellaneous nitrogen compounds.

Authors:  R F NYSTROM; W G BROWN
Journal:  J Am Chem Soc       Date:  1948-11       Impact factor: 15.419

4.  (1-Pyrenylmethyl)amino alcohols, a new class of antitumor DNA intercalators. Discovery and initial amine side chain structure-activity studies.

Authors:  K W Bair; R L Tuttle; V C Knick; M Cory; D D McKee
Journal:  J Med Chem       Date:  1990-09       Impact factor: 7.446

5.  Synthesis, characterization, and energetic properties of diazido heteroaromatic high-nitrogen C-N compound.

Authors:  My Hang V Huynh; Michael A Hiskey; David E Chavez; Darren L Naud; Richard D Gilardi
Journal:  J Am Chem Soc       Date:  2005-09-14       Impact factor: 15.419

6.  Design, Synthesis, and in Vitro Evaluation of Novel Aminomethyl-pyridines as DPP-4 Inhibitors.

Authors:  Katarzyna Kaczanowska; Karl-Heinz Wiesmüller; Arnaud-Pierre Schaffner
Journal:  ACS Med Chem Lett       Date:  2010-10-05       Impact factor: 4.345

Review 7.  Regioselective (site-selective) functionalization of unsaturated halogenated nitrogen, oxygen and sulfur heterocycles by Pd-catalysed cross-couplings and direct arylation processes.

Authors:  Ian J S Fairlamb
Journal:  Chem Soc Rev       Date:  2007-04-27       Impact factor: 54.564

8.  Expeditious total syntheses of camptothecin and 10-hydroxycamptothecin.

Authors:  Guan-Sai Liu; Qing-Li Dong; Yuan-Shan Yao; Zhu-Jun Yao
Journal:  Org Lett       Date:  2008-12-04       Impact factor: 6.005

9.  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

10.  Treatment of cellulitis with ceforanide.

Authors:  D M Musher; V Fainstein; E J Young
Journal:  Antimicrob Agents Chemother       Date:  1980-02       Impact factor: 5.191

View more
  10 in total

1.  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

2.  Rapid and efficient access to secondary arylmethylamines.

Authors:  Nicolas Fleury-Brégeot; Jessica Raushel; Deidre L Sandrock; Spencer D Dreher; Gary A Molander
Journal:  Chemistry       Date:  2012-07-05       Impact factor: 5.236

3.  A Dual-Modality Linker Enables Site-Specific Conjugation of Antibody Fragments for 18F-Immuno-PET and Fluorescence Imaging.

Authors:  Kirstin A Zettlitz; Christopher M Waldmann; Wen-Ting K Tsai; Richard Tavaré; Jeffrey Collins; Jennifer M Murphy; Anna M Wu
Journal:  J Nucl Med       Date:  2019-03-15       Impact factor: 10.057

4.  Suzuki-Miyaura cross-coupling reactions of potassium Boc-protected aminomethyltrifluoroborate with aryl and hetaryl mesylates.

Authors:  Gary A Molander; Inji Shin
Journal:  Org Lett       Date:  2012-05-31       Impact factor: 6.005

5.  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

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

Authors:  Gary A Molander; Inji Shin
Journal:  Org Lett       Date:  2013-05-06       Impact factor: 6.005

7.  Suzuki-Miyaura cross-coupling of potassium alkoxyethyltrifluoroborates: access to aryl/heteroarylethyloxy motifs.

Authors:  Nicolas Fleury-Brégeot; Marc Presset; Floriane Beaumard; Virginie Colombel; Daniel Oehlrich; Frederik Rombouts; Gary A Molander
Journal:  J Org Chem       Date:  2012-11-06       Impact factor: 4.354

Review 8.  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

9.  Synthesis and biological evaluation of indolyl-pyridinyl-propenones having either methuosis or microtubule disruption activity.

Authors:  Christopher J Trabbic; Jean H Overmeyer; Evan M Alexander; Emily J Crissman; Heather M Kvale; Marcie A Smith; Paul W Erhardt; William A Maltese
Journal:  J Med Chem       Date:  2015-02-19       Impact factor: 7.446

10.  An Integrated Approach toward NanoBRET Tracers for Analysis of GPCR Ligand Engagement.

Authors:  Michael P Killoran; Sergiy Levin; Michelle E Boursier; Kristopher Zimmerman; Robin Hurst; Mary P Hall; Thomas Machleidt; Thomas A Kirkland; Rachel Friedman Ohana
Journal:  Molecules       Date:  2021-05-12       Impact factor: 4.411

  10 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.