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Literature DB >> 29745674

Transforming Benzylic Amines into Diarylmethanes: Cross-Couplings of Benzylic Pyridinium Salts via C-N Bond Activation.

Jennie Liao¹, Weiye Guan¹, Brian P Boscoe², Joseph W Tucker², John W Tomlin¹, Michelle R Garnsey², Mary P Watson¹.

Abstract

A nickel-catalyzed cross-coupling of benzylic pyridinium salts with arylboronic acids was developed. Coupled with chemoselective pyridinium formation, this method allows benzyl primary amines to be efficiently converted to di(hetero)arylmethanes. Excellent heteroaryl and functional group tolerance is observed, and a one-pot procedure enables benzylic amines to be converted to diarylmethanes directly.

Entities: Chemical Disease Gene

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Year: 2018 PMID： 29745674 PMCID： PMC6005208 DOI： 10.1021/acs.orglett.8b01062

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

55 in total

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Authors: J Xu; J Stevenson
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2. A General, Simple Catalyst for Enantiospecific Cross Couplings of Benzylic Ammonium Triflates and Boronic Acids: No Phosphine Ligand Required.

Authors: Danielle M Shacklady-McAtee; Kelsey M Roberts; Corey H Basch; Ye-Geun Song; Mary P Watson
Journal: Tetrahedron Date: 2014-07-08 Impact factor: 2.457

3. N-vinylpyridinium and -ammonium tetrafluoroborate salts: new electrophilic coupling partners for Pd(0)-catalyzed Suzuki cross-coupling reactions.

Authors: Keith R Buszek; Neil Brown
Journal: Org Lett Date: 2007-01-25 Impact factor: 6.005

4. Direct benzylic alkylation via Ni-catalyzed selective benzylic sp3 C-O activation.

Authors: Bing-Tao Guan; Shi-Kai Xiang; Bi-Qin Wang; Zuo-Peng Sun; Yang Wang; Ke-Qing Zhao; Zhang-Jie Shi
Journal: J Am Chem Soc Date: 2008-02-26 Impact factor: 15.419

5. Metal-free sp(3) C-H functionalization: a novel approach for the syntheses of selenide ethers and thioesters from methyl arenes.

Authors: Satpal Singh Badsara; Yi-Chen Liu; Ping-An Hsieh; Jing-Wen Zeng; Shao-Yi Lu; Yi-Wei Liu; Chin-Fa Lee
Journal: Chem Commun (Camb) Date: 2014-10-07 Impact factor: 6.222

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Authors: A K Ghose; V N Viswanadhan; J J Wendoloski
Journal: J Comb Chem Date: 1999-01

7. 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

8. 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

9. Entrectinib is a potent inhibitor of Trk-driven neuroblastomas in a xenograft mouse model.

Authors: Radhika Iyer; Lea Wehrmann; Rebecca L Golden; Koumudi Naraparaju; Jamie L Croucher; Suzanne P MacFarland; Peng Guan; Venkatadri Kolla; Ge Wei; Nicholas Cam; Gang Li; Zachary Hornby; Garrett M Brodeur
Journal: Cancer Lett Date: 2016-01-18 Impact factor: 8.679

Transforming Benzylic Amines into Diarylmethanes: Cross-Couplings of Benzylic Pyridinium Salts via C-N Bond Activation.

1. Drug-like index: a new approach to measure drug-like compounds and their diversity.

2. A General, Simple Catalyst for Enantiospecific Cross Couplings of Benzylic Ammonium Triflates and Boronic Acids: No Phosphine Ligand Required.

3. N-vinylpyridinium and -ammonium tetrafluoroborate salts: new electrophilic coupling partners for Pd(0)-catalyzed Suzuki cross-coupling reactions.

4. Direct benzylic alkylation via Ni-catalyzed selective benzylic sp3 C-O activation.

5. Metal-free sp(3) C-H functionalization: a novel approach for the syntheses of selenide ethers and thioesters from methyl arenes.

6. A knowledge-based approach in designing combinatorial or medicinal chemistry libraries for drug discovery. 1. A qualitative and quantitative characterization of known drug databases.

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

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

9. Entrectinib is a potent inhibitor of Trk-driven neuroblastomas in a xenograft mouse model.

10. Nickel-catalyzed cross-couplings of organosilicon reagents with unactivated secondary alkyl bromides.

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

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

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

4. Deaminative Reductive Cross-Electrophile Couplings of Alkylpyridinium Salts and Aryl Bromides.

Review 5. Recent Progress in Fragmentation of Katritzky Salts Enabling Formation of C-C, C-B, and C-S Bonds.

6. Tunable and Practical Homogeneous Organic Reductants for Cross-Electrophile Coupling.

7. Site-Selective Synthesis of N-Benzyl 2,4,6-Collidinium Salts by Electrooxidative C-H Functionalization.

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

9. Harnessing Alkylpyridinium Salts as Electrophiles in Deaminative Alkyl-Alkyl Cross-Couplings.

10. Phosphite mediated asymmetric N to C migration for the synthesis of chiral heterocycles from primary amines.