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Literature DB >> 30174353

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

Weiye Guan¹, Jennie Liao¹, Mary P Watson¹.

Abstract

Cross-couplings of benzylic pyridinium salts and vinylboronic acids or esters have been developed. Via these benzylic pyridinium intermediates, benzylic amines can be engaged in these cross-couplings via C-N bond functionalization. This method boasts mild reaction conditions and excellent tolerance for heteroaryl substituents and a range of functional groups.

Entities: CellLine Chemical Disease Gene

Keywords: allyl complexes; amines; benzylation; catalysis; cross-coupling; nickel

Year: 2018 PMID： 30174353 PMCID： PMC6112771 DOI： 10.1055/s-0037-1610084

Source DB: PubMed Journal: Synthesis (Stuttg) ISSN： 0039-7881 Impact factor: 3.157

46 in total

1. Rhodium-catalyzed cross-coupling of allyl alcohols with aryl- and vinylboronic acids in ionic liquids.

Authors: George W Kabalka; Gang Dong; Bollu Venkataiah
Journal: Org Lett Date: 2003-03-20 Impact factor: 6.005

2. 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

3. Suzuki-Miyaura cross-coupling of benzylic carbonates with arylboronic acids.

Authors: Ryoichi Kuwano; Masashi Yokogi
Journal: Org Lett Date: 2005-03-03 Impact factor: 6.005

4. 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

5. Simple (imidazol-2-ylidene)-Pd-acetate complexes as effective precatalysts for sterically hindered Suzuki-Miyaura couplings.

Authors: Rohit Singh; Mihai S Viciu; Natalia Kramareva; Oscar Navarro; Steven P Nolan
Journal: Org Lett Date: 2005-04-28 Impact factor: 6.005

6. Palladium-catalyzed cross-coupling reactions of organogold(I) reagents with organic electrophiles.

Authors: Miguel Peña-López; Miguel Ayán-Varela; Luis A Sarandeses; José Pérez Sestelo
Journal: Chemistry Date: 2010-08-23 Impact factor: 5.236

7. Preparation of Solid, Substituted Allylic Zinc Reagents and Their Reactions with Electrophiles.

Authors: Mario Ellwart; Paul Knochel
Journal: Angew Chem Int Ed Engl Date: 2015-07-17 Impact factor: 15.336

8. Transition-Metal-Free Stereospecific Cross-Coupling with Alkenylboronic Acids as Nucleophiles.

Authors: Chengxi Li; Yuanyuan Zhang; Qi Sun; Tongnian Gu; Henian Peng; Wenjun Tang
Journal: J Am Chem Soc Date: 2016-08-17 Impact factor: 15.419

9. Transition metal catalyzed nucleophilic allylic substitution: activation of allylic alcohols via π-allylic species.

Authors: Basker Sundararaju; Mathieu Achard; Christian Bruneau
Journal: Chem Soc Rev Date: 2012-05-10 Impact factor: 54.564

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

Authors: Jennie Liao; Weiye Guan; Brian P Boscoe; Joseph W Tucker; John W Tomlin; Michelle R Garnsey; Mary P Watson
Journal: Org Lett Date: 2018-05-10 Impact factor: 6.005

12 in total

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

1. Rhodium-catalyzed cross-coupling of allyl alcohols with aryl- and vinylboronic acids in ionic liquids.

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

3. Suzuki-Miyaura cross-coupling of benzylic carbonates with arylboronic acids.

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

5. Simple (imidazol-2-ylidene)-Pd-acetate complexes as effective precatalysts for sterically hindered Suzuki-Miyaura couplings.

6. Palladium-catalyzed cross-coupling reactions of organogold(I) reagents with organic electrophiles.

7. Preparation of Solid, Substituted Allylic Zinc Reagents and Their Reactions with Electrophiles.

8. Transition-Metal-Free Stereospecific Cross-Coupling with Alkenylboronic Acids as Nucleophiles.

9. Transition metal catalyzed nucleophilic allylic substitution: activation of allylic alcohols via π-allylic species.

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

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

Review 4. Recent Progress in Fragmentation of Katritzky Salts Enabling Formation of C-C, C-B, and C-S Bonds.

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

6. Deaminative Reductive Methylation of Alkylpyridinium Salts.

7. Dissection of Alkylpyridinium Structures to Understand Deamination Reactions.

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. Catalyst-Free Deaminative Functionalizations of Primary Amines by Photoinduced Single-Electron Transfer.