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Literature DB >> 22360350

Synthesis of functionalized dialkyl ketones from carboxylic acid derivatives and alkyl halides.

Abstract

Unsymmetrical dialkyl ketones can be directly prepared by the nickel-catalyzed reductive coupling of carboxylic acid chlorides or (2-pyridyl)thioesters with alkyl iodides or benzylic chlorides. A wide variety of functional groups are tolerated by this process, including common nitrogen protecting groups and C-B bonds. Even hindered ketones flanked by tertiary and secondary centers can be formed. The mechanism is proposed to involve the reaction of a (L)Ni(alkyl)(2) intermediate with the carboxylic acid derivative.

Entities: Chemical Disease

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Year: 2012 PMID： 22360350 PMCID： PMC3308727 DOI： 10.1021/ol300217x

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

18 in total

Review 1. Choosing an effective protein bioconjugation strategy.

Authors: Nicholas Stephanopoulos; Matthew B Francis
Journal: Nat Chem Biol Date: 2011-11-15 Impact factor: 15.040

2. Development of trifunctional probes for glycoproteomic analysis.

Authors: Charng-Sheng Tsai; Po-Yu Liu; Hsin-Yung Yen; Tsui-Ling Hsu; Chi-Huey Wong
Journal: Chem Commun (Camb) Date: 2010-05-13 Impact factor: 6.222

3. Synthesis of a biotin-derived alkyne for pd-catalyzed coupling reactions.

Authors: Cesear Corona; Bj K Bryant; Jeffrey B Arterburn
Journal: Org Lett Date: 2006-04-27 Impact factor: 6.005

4. 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

5. Trifunctional chemical probes for the consolidated detection and identification of enzyme activities from complex proteomes.

Authors: Gregory C Adam; Erik J Sorensen; Benjamin F Cravatt
Journal: Mol Cell Proteomics Date: 2002-10 Impact factor: 5.911

6. A unique catalyst effects the rapid room-temperature cross-coupling of organozinc reagents with carboxylic acid fluorides, chlorides, anhydrides, and thioesters.

Authors: Yongda Zhang; Tomislav Rovis
Journal: J Am Chem Soc Date: 2004-12-15 Impact factor: 15.419

7. Nickel-catalyzed reductive cross-coupling of aryl halides with alkyl halides.

Authors: Daniel A Everson; Ruja Shrestha; Daniel J Weix
Journal: J Am Chem Soc Date: 2010-01-27 Impact factor: 15.419

8. Synthesis of high enantiopurity N-protected alpha-amino ketones by thiol ester-organostannane cross-coupling using pH-neutral conditions.

Authors: Hao Li; Hao Yang; Lanny S Liebeskind
Journal: Org Lett Date: 2008-08-30 Impact factor: 6.005

9. Palladium-catalyzed cross-coupling reactions of carboxylic anhydrides with organozinc reagents.

Authors: Donghui Wang; Zhaoguo Zhang
Journal: Org Lett Date: 2003-11-27 Impact factor: 6.005

10. Bioorthogonal chemistry: fishing for selectivity in a sea of functionality.

Authors: Ellen M Sletten; Carolyn R Bertozzi
Journal: Angew Chem Int Ed Engl Date: 2009 Impact factor: 15.336

26 in total

1. Nickel-Catalyzed Asymmetric Reductive Cross-Coupling To Access 1,1-Diarylalkanes.

Authors: Kelsey E Poremba; Nathaniel T Kadunce; Naoyuki Suzuki; Alan H Cherney; Sarah E Reisman
Journal: J Am Chem Soc Date: 2017-04-13 Impact factor: 15.419

2. Catalytic Conjunctive Coupling of Carboxylic Acid Derivatives with 9-BBN-Derived Ate Complexes.

Authors: Chunyin Law; Yan Meng; Seung Moh Koo; James P Morken
Journal: Angew Chem Int Ed Engl Date: 2019-04-04 Impact factor: 15.336

3. A Radical Approach to Anionic Chemistry: Synthesis of Ketones, Alcohols, and Amines.

Authors: Shengyang Ni; Natalia M Padial; Cian Kingston; Julien C Vantourout; Daniel C Schmitt; Jacob T Edwards; Monika M Kruszyk; Rohan R Merchant; Pavel K Mykhailiuk; Brittany B Sanchez; Shouliang Yang; Matthew A Perry; Gary M Gallego; James J Mousseau; Michael R Collins; Robert J Cherney; Pavlo S Lebed; Jason S Chen; Tian Qin; Phil S Baran
Journal: J Am Chem Soc Date: 2019-04-16 Impact factor: 15.419

Synthesis of functionalized dialkyl ketones from carboxylic acid derivatives and alkyl halides.

Review 1. Choosing an effective protein bioconjugation strategy.

2. Development of trifunctional probes for glycoproteomic analysis.

3. Synthesis of a biotin-derived alkyne for pd-catalyzed coupling reactions.

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

5. Trifunctional chemical probes for the consolidated detection and identification of enzyme activities from complex proteomes.

6. A unique catalyst effects the rapid room-temperature cross-coupling of organozinc reagents with carboxylic acid fluorides, chlorides, anhydrides, and thioesters.

7. Nickel-catalyzed reductive cross-coupling of aryl halides with alkyl halides.

8. Synthesis of high enantiopurity N-protected alpha-amino ketones by thiol ester-organostannane cross-coupling using pH-neutral conditions.

9. Palladium-catalyzed cross-coupling reactions of carboxylic anhydrides with organozinc reagents.

10. Bioorthogonal chemistry: fishing for selectivity in a sea of functionality.

1. Nickel-Catalyzed Asymmetric Reductive Cross-Coupling To Access 1,1-Diarylalkanes.

2. Catalytic Conjunctive Coupling of Carboxylic Acid Derivatives with 9-BBN-Derived Ate Complexes.

3. A Radical Approach to Anionic Chemistry: Synthesis of Ketones, Alcohols, and Amines.

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

5. Copper-Catalyzed Borylacylation of Activated Alkenes with Acid Chlorides.

6. Cross-Coupling and Related Reactions: Connecting Past Success to the Development of New Reactions for the Future.

7. Ketones from Nickel-Catalyzed Decarboxylative, Non-Symmetric Cross-Electrophile Coupling of Carboxylic Acid Esters.

8. Nickel-Catalyzed Synthesis of Ketones from Alkyl Halides and Acid Chlorides: Preparation of Ethyl 4-Oxododecanoate.

9. Direct C-C Bond Formation from Alkanes Using Ni-Photoredox Catalysis.

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