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Literature DB >> 31763855

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

Kristen M Baker¹, Diana Lucas Baca¹, Shane Plunkett¹, Mitchell E Daneker¹, Mary P Watson¹.

Abstract

An alkyl-alkyl cross-coupling of Katritzky alkylpyridinium salts and organoboranes, formed in situ via hydroboration of alkenes, has been developed. This method utilizes the abundance of both alkyl amine precursors and alkenes to form C(sp3)-C(sp3) bonds. This strategy is also effective with alkynes, enabling a C(sp3)-C(sp2) cross-coupling. Under these mild conditions, a broad range of functional groups, including protic groups, is tolerated. As seen with previous alkylpyridinium cross-couplings, mechanistic studies support an alkyl radical intermediate.

Entities: Chemical Gene Species

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Year: 2019 PMID： 31763855 PMCID： PMC6933946 DOI： 10.1021/acs.orglett.9b03899

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

22 in total

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

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

2. Visible-Light-Mediated Charge Transfer Enables C-C Bond Formation with Traceless Acceptor Groups.

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

4. Deaminative Reductive Arylation Enabled by Nickel/Photoredox Dual Catalysis.

Review 5. Applications of Palladium-Catalyzed C-N Cross-Coupling Reactions.

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

7. Deaminative Strategy for the Visible-Light-Mediated Generation of Alkyl Radicals.

8. Photoinduced Deaminative Borylation of Alkylamines.

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

10. Nickel-catalyzed C-N bond activation: activated primary amines as alkylating reagents in reductive cross-coupling.

Review 1. Recent Progress in Fragmentation of Katritzky Salts Enabling Formation of C-C, C-B, and C-S Bonds.

2. Dual Nickel/Photoredox-Catalyzed Deaminative Cross-Coupling of Sterically Hindered Primary Amines.

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

4. Deaminative Reductive Methylation of Alkylpyridinium Salts.

5. α-Chiral Amines via Thermally Promoted Deaminative Addition of Alkylpyridinium Salts to Sulfinimines.

6. Deoxygenative α-alkylation and α-arylation of 1,2-dicarbonyls.