Literature DB >> 28359153

Harnessing Alkyl Amines as Electrophiles for Nickel-Catalyzed Cross Couplings via C-N Bond Activation.

Corey H Basch1, Jennie Liao1, Jianyu Xu1, Jacob J Piane1, Mary P Watson1.   

Abstract

We developed a strategy to harness alkyl amines as alkylating agents via C-N bond activation. This Suzuki-Miyaura cross coupling of alkylpyridinium salts, readily formed from primary amines, is the first example of a metal-catalyzed cross coupling via C-N bond activation of an amine with an unactivated alkyl group. This reaction enjoys broad scope and functional group tolerance. Primary and secondary alkyl groups can be installed. Preliminary studies suggest a NiI/NiIII catalytic cycle.

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Year:  2017        PMID： 28359153      PMCID： PMC5480296          DOI： 10.1021/jacs.7b02389

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  86 in total

Review 1.  Transition-Metal-Catalyzed Cleavage of C-N Single Bonds.

Authors:  Kunbing Ouyang; Wei Hao; Wen-Xiong Zhang; Zhenfeng Xi
Journal:  Chem Rev       Date:  2015-10-01       Impact factor: 60.622

2.  Amino alcohols as ligands for nickel-catalyzed suzuki reactions of unactivated alkyl halides, including secondary alkyl chlorides, with arylboronic acids.

Authors:  Francisco González-Bobes; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2006-04-26       Impact factor: 15.419

3.  Nickel-catalyzed cross-coupling of aryl bromides with tertiary Grignard reagents utilizing donor-functionalized N-heterocyclic carbenes (NHCs).

Authors:  Claudia Lohre; Thomas Dröge; Congyang Wang; Frank Glorius
Journal:  Chemistry       Date:  2011-04-20       Impact factor: 5.236

4.  Engaging nonaromatic, heterocyclic tosylates in reductive cross-coupling with aryl and heteroaryl bromides.

Authors:  Gary A Molander; Kaitlin M Traister; Brian T O'Neill
Journal:  J Org Chem       Date:  2015-02-25       Impact factor: 4.354

5.  Making Dimethylamino a Transformable Directing Group by Nickel-Catalyzed C-N Borylation.

Authors:  Hua Zhang; Shinya Hagihara; Kenichiro Itami
Journal:  Chemistry       Date:  2015-10-05       Impact factor: 5.236

6.  Chiral N-alkyl-2,4,6-triphenylpyridiniums as enantioselective triplet photosensitizers. laser flash photolysis and preparative studies.

Authors:  Mercedes Alvaro; Pilar Formentín; Hermenegildo García; Emilio Palomares; María J Sabater
Journal:  J Org Chem       Date:  2002-07-26       Impact factor: 4.354

7.  Density functional theory studies of negishi alkyl-alkyl cross-coupling reactions catalyzed by a methylterpyridyl-Ni(I) complex.

Authors:  Xufeng Lin; David Lee Phillips
Journal:  J Org Chem       Date:  2008-04-15       Impact factor: 4.354

8.  C(sp3)-C(sp2) cross-coupling of alkylsilicates with borylated aryl bromides - an iterative platform to alkylated aryl- and heteroaryl boronates.

Authors:  Brandon A Vara; Matthieu Jouffroy; Gary A Molander
Journal:  Chem Sci       Date:  2016-09-09       Impact factor: 9.825

9.  Phenol Derivatives as Coupling Partners with Alkylsilicates in Photoredox/Nickel Dual Catalysis.

Authors:  Niki R Patel; Gary A Molander
Journal:  J Org Chem       Date:  2016-06-03       Impact factor: 4.354

Review 10.  Recent developments in the Suzuki-Miyaura reaction: 2010-2014.

Authors:  Irene Maluenda; Oscar Navarro
Journal:  Molecules       Date:  2015-04-24       Impact factor: 4.411
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  41 in total

1.  Engaging Alkenes and Alkynes in Deaminative Alkyl-Alkyl and Alkyl-Vinyl Cross-Couplings of Alkylpyridinium Salts.

Authors:  Kristen M Baker; Diana Lucas Baca; Shane Plunkett; Mitchell E Daneker; Mary P Watson
Journal:  Org Lett       Date:  2019-11-25       Impact factor: 6.005

2.  Photoredox-Mediated Net-Neutral Radical/Polar Crossover Reactions.

Authors:  Rebecca J Wiles; Gary A Molander
Journal:  Isr J Chem       Date:  2020-02-18       Impact factor: 3.333

3.  Deaminative Arylation of Amino Acid-derived Pyridinium Salts.

Authors:  Megan E Hoerrner; Kristen M Baker; Corey H Basch; Earl M Bampo; Mary P Watson
Journal:  Org Lett       Date:  2019-08-29       Impact factor: 6.005

4.  Synthesis of β-Phenethylamines via Ni/Photoredox Cross-Electrophile Coupling of Aliphatic Aziridines and Aryl Iodides.

Authors:  Talia J Steiman; Junyi Liu; Amanuella Mengiste; Abigail G Doyle
Journal:  J Am Chem Soc       Date:  2020-04-06       Impact factor: 15.419

Review 5.  Cross-Coupling of Heteroatomic Electrophiles.

Authors:  Katerina M Korch; Donald A Watson
Journal:  Chem Rev       Date:  2019-06-11       Impact factor: 60.622

6.  Selective Modification of Tryptophan Residues in Peptides and Proteins Using a Biomimetic Electron Transfer Process.

Authors:  Samantha J Tower; Wesley J Hetcher; Tyler E Myers; Nicholas J Kuehl; Michael T Taylor
Journal:  J Am Chem Soc       Date:  2020-05-05       Impact factor: 15.419

7.  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

8.  Mechanistic Interrogation of Co/Ni-Dual Catalyzed Hydroarylation.

Authors:  Sophia L Shevick; Carla Obradors; Ryan A Shenvi
Journal:  J Am Chem Soc       Date:  2018-09-18       Impact factor: 15.419

9.  Vinylation of Benzylic Amines via C-N Bond Functionalization of Benzylic Pyridinium Salts.

Authors:  Weiye Guan; Jennie Liao; Mary P Watson
Journal:  Synthesis (Stuttg)       Date:  2018-06-08       Impact factor: 3.157

10.  Asymmetric synthesis via stereospecific C-N and C-O bond activation of alkyl amine and alcohol derivatives.

Authors:  Sarah M Pound; Mary P Watson
Journal:  Chem Commun (Camb)       Date:  2018-10-30       Impact factor: 6.222
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