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Literature DB >> 24795502

Nickel-catalyzed cross-electrophile coupling of 2-chloropyridines with alkyl bromides.

Daniel A Everson¹, Joseph A Buonomo¹, Daniel J Weix¹.

Abstract

The synthesis of 2-alkylated pyridines by the nickel-catalyzed cross-coupling of two different electrophiles, 2-chloropyridines with alkyl bromides, is described. Compared to our previously published conditions for aryl halides, this method uses the different, more rigid bathophenanthroline ligand and is conducted at high concentration in DMF solvent. The method displays promising functional group compatibility and the conditions are orthogonal to the Stille coupling.

Entities: Chemical Disease Gene

Keywords: Nickel; catalysis; cross-coupling; electrophile; pyridine

Year: 2014 PMID： 24795502 PMCID： PMC4006914 DOI： 10.1055/s-0033-1340151

Source DB: PubMed Journal: Synlett ISSN： 0936-5214 Impact factor: 2.454

35 in total

1. Direct method for carbon-carbon bond formation: the functional group tolerant cobalt-catalyzed alkylation of aryl halides.

Authors: Muriel Amatore; Corinne Gosmini
Journal: Chemistry Date: 2010-05-25 Impact factor: 5.236

2. Analysis of key steps in the catalytic cross-coupling of alkyl electrophiles under Negishi-like conditions.

Authors: Gavin D Jones; Chris McFarland; Thomas J Anderson; David A Vicic
Journal: Chem Commun (Camb) Date: 2005-07-22 Impact factor: 6.222

3. Reductive conjugate addition of haloalkanes to enones to form silyl enol ethers.

Authors: Ruja Shrestha; Daniel J Weix
Journal: Org Lett Date: 2011-04-14 Impact factor: 6.005

4. Nickel-mediated inter- and intramolecular reductive cross-coupling of unactivated alkyl bromides and aryl iodides at room temperature.

Authors: Chang-Song Yan; Yu Peng; Xiao-Bo Xu; Ya-Wen Wang
Journal: Chemistry Date: 2012-03-30 Impact factor: 5.236

5. Mild ketone formation via Ni-catalyzed reductive coupling of unactivated alkyl halides with acid anhydrides.

Authors: Hongyu Yin; Chenglong Zhao; Hengzhi You; Kunhua Lin; Hegui Gong
Journal: Chem Commun (Camb) Date: 2012-06-11 Impact factor: 6.222

6. Nickel-catalyzed reductive cross-coupling of unactivated alkyl halides.

Authors: Xiaolong Yu; Tao Yang; Shulin Wang; Hailiang Xu; Hegui Gong
Journal: Org Lett Date: 2011-03-24 Impact factor: 6.005

7. Ketone formation via mild nickel-catalyzed reductive coupling of alkyl halides with aryl acid chlorides.

Authors: Fan Wu; Wenbin Lu; Qun Qian; Qinghua Ren; Hegui Gong
Journal: Org Lett Date: 2012-05-31 Impact factor: 6.005

8. Ni-catalyzed reductive allylation of unactivated alkyl halides with allylic carbonates.

Authors: Yijing Dai; Fan Wu; Zhenhua Zang; Hengzhi You; Hegui Gong
Journal: Chemistry Date: 2011-12-14 Impact factor: 5.236

9. 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

10. Functional group tolerant Kumada-Corriu-Tamao coupling of nonactivated alkyl halides with aryl and heteroaryl nucleophiles: catalysis by a nickel pincer complex permits the coupling of functionalized Grignard reagents.

Authors: Oleg Vechorkin; Valérie Proust; Xile Hu
Journal: J Am Chem Soc Date: 2009-07-22 Impact factor: 15.419

11 in total

Nickel-catalyzed cross-electrophile coupling of 2-chloropyridines with alkyl bromides.

1. Direct method for carbon-carbon bond formation: the functional group tolerant cobalt-catalyzed alkylation of aryl halides.

2. Analysis of key steps in the catalytic cross-coupling of alkyl electrophiles under Negishi-like conditions.

3. Reductive conjugate addition of haloalkanes to enones to form silyl enol ethers.

4. Nickel-mediated inter- and intramolecular reductive cross-coupling of unactivated alkyl bromides and aryl iodides at room temperature.

5. Mild ketone formation via Ni-catalyzed reductive coupling of unactivated alkyl halides with acid anhydrides.

6. Nickel-catalyzed reductive cross-coupling of unactivated alkyl halides.

7. Ketone formation via mild nickel-catalyzed reductive coupling of alkyl halides with aryl acid chlorides.

8. Ni-catalyzed reductive allylation of unactivated alkyl halides with allylic carbonates.

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

10. Functional group tolerant Kumada-Corriu-Tamao coupling of nonactivated alkyl halides with aryl and heteroaryl nucleophiles: catalysis by a nickel pincer complex permits the coupling of functionalized Grignard reagents.

1. Exhaustive Suzuki-Miyaura reactions of polyhalogenated heteroarenes with alkyl boronic pinacol esters.

2. The Power of Chemists Is in What They Can Learn, Not What They Already Know.

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

4. Nickel-Catalyzed Asymmetric Reductive Cross-Coupling between Heteroaryl Iodides and α-Chloronitriles.

5. Methods and Mechanisms for Cross-Electrophile Coupling of Csp(2) Halides with Alkyl Electrophiles.

6. Coupling of Challenging Heteroaryl Halides with Alkyl Halides via Nickel-Catalyzed Cross-Electrophile Coupling.

7. Selective and Serial Suzuki-Miyaura Reactions of Polychlorinated Aromatics with Alkyl Pinacol Boronic Esters.

8. A mild catalytic system for radical conjugate addition of nitrogen heterocycles.

9. Nickel-Catalyzed Reductive Conjugate Addition of Primary Alkyl Bromides to Enones To Form Silyl Enol Ethers.

10. Cross-electrophile coupling: principles of reactivity and selectivity.