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Literature DB >> 27043656

Tandem Rh-catalysis: decarboxylative β-keto acid and alkyne cross-coupling.

Faben A Cruz¹, Zhiwei Chen, Sarah I Kurtoic, Vy M Dong.

Abstract

Herein, we describe a regioselective Rh-catalyzed decarboxylative cross-coupling of β-keto acids and alkynes to access branched γ,δ-unsaturated ketones. Rh-hydride catalysis enables the isomerization of an alkyne to generate a metal-allyl species that can undergo carbon-carbon bond formation. Ketones are generated under mild conditions, without the need for base or activated electrophiles.

Entities: Chemical Gene

Mesh：

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Year: 2016 PMID： 27043656 PMCID： PMC4851867 DOI： 10.1039/c6cc02522f

Source DB: PubMed Journal: Chem Commun (Camb) ISSN： 1359-7345 Impact factor: 6.222

65 in total

1. Asymmetric transition-metal-catalyzed allylic alkylations: applications in total synthesis.

Authors: Barry M Trost; Matthew L Crawley
Journal: Chem Rev Date: 2003-08 Impact factor: 60.622

2. Stereoelectronic effects dictate mechanistic dichotomy between Cu(II)-catalyzed and enzyme-catalyzed reactions of malonic acid half thioesters.

Authors: Kevin C Fortner; Matthew D Shair
Journal: J Am Chem Soc Date: 2007-02-07 Impact factor: 15.419

3. Mechanistically driven development of iridium catalysts for asymmetric allylic substitution.

Authors: John F Hartwig; Levi M Stanley
Journal: Acc Chem Res Date: 2010-09-28 Impact factor: 22.384

4. Redox-neutral atom-economic rhodium-catalyzed coupling of terminal alkynes with carboxylic acids toward branched allylic esters.

Authors: Alexandre Lumbroso; Philipp Koschker; Nicolas R Vautravers; Bernhard Breit
Journal: J Am Chem Soc Date: 2011-02-03 Impact factor: 15.419

5. Rhodium-catalyzed chemo- and regioselective decarboxylative addition of β-ketoacids to allenes: efficient construction of tertiary and quaternary carbon centers.

Authors: Changkun Li; Bernhard Breit
Journal: J Am Chem Soc Date: 2014-01-09 Impact factor: 15.419

6. Dual catalysis. Merging photoredox with nickel catalysis: coupling of α-carboxyl sp³-carbons with aryl halides.

Authors: Zhiwei Zuo; Derek T Ahneman; Lingling Chu; Jack A Terrett; Abigail G Doyle; David W C MacMillan
Journal: Science Date: 2014-06-05 Impact factor: 47.728

7. Iridium-catalyzed regioselective decarboxylative allylation of β-ketoacids: efficient construction of γ,δ-unsaturated ketones.

Authors: Shu-Jie Chen; Guo-Ping Lu; Chun Cai
Journal: Chem Commun (Camb) Date: 2015-07-21 Impact factor: 6.222

8. Merging Photoredox and Nickel Catalysis: The Direct Synthesis of Ketones by the Decarboxylative Arylation of α-Oxo Acids.

Authors: Lingling Chu; Jeffrey M Lipshultz; David W C MacMillan
Journal: Angew Chem Int Ed Engl Date: 2015-05-26 Impact factor: 15.336

9. Control of diastereoselectivity for iridium-catalyzed allylation of a prochiral nucleophile with a phosphate counterion.

Authors: Wenyong Chen; John F Hartwig
Journal: J Am Chem Soc Date: 2013-01-30 Impact factor: 15.419

Tandem Rh-catalysis: decarboxylative β-keto acid and alkyne cross-coupling.

1. Asymmetric transition-metal-catalyzed allylic alkylations: applications in total synthesis.

2. Stereoelectronic effects dictate mechanistic dichotomy between Cu(II)-catalyzed and enzyme-catalyzed reactions of malonic acid half thioesters.

3. Mechanistically driven development of iridium catalysts for asymmetric allylic substitution.

4. Redox-neutral atom-economic rhodium-catalyzed coupling of terminal alkynes with carboxylic acids toward branched allylic esters.

5. Rhodium-catalyzed chemo- and regioselective decarboxylative addition of β-ketoacids to allenes: efficient construction of tertiary and quaternary carbon centers.

6. Dual catalysis. Merging photoredox with nickel catalysis: coupling of α-carboxyl sp³-carbons with aryl halides.

7. Iridium-catalyzed regioselective decarboxylative allylation of β-ketoacids: efficient construction of γ,δ-unsaturated ketones.

8. Merging Photoredox and Nickel Catalysis: The Direct Synthesis of Ketones by the Decarboxylative Arylation of α-Oxo Acids.

9. Control of diastereoselectivity for iridium-catalyzed allylation of a prochiral nucleophile with a phosphate counterion.

10. Carboxylic acids as a traceless activation group for conjugate additions: a three-step synthesis of (±)-pregabalin.

1. Enantioselective Intermolecular Pd-Catalyzed Hydroalkylation of Acyclic 1,3-Dienes with Activated Pronucleophiles.

2. Alkyne Hydroheteroarylation: Enantioselective Coupling of Indoles and Alkynes via Rh-Hydride Catalysis.

Review 3. Alkynes as Electrophilic or Nucleophilic Allylmetal Precursors in Transition-Metal Catalysis.

4. Rhodium-Catalyzed Hydrofunctionalization: Enantioselective Coupling of Indolines and 1,3-Dienes.

5. Enantioselective Addition of α-Nitroesters to Alkynes.

6. Stereodivergent Coupling of Aldehydes and Alkynes via Synergistic Catalysis Using Rh and Jacobsen's Amine.

7. Reducing Challenges in Organic Synthesis with Stereoselective Hydrogenation and Tandem Catalysis.

8. Brønsted acid and Pd-PHOX dual-catalysed enantioselective addition of activated C-pronucleophiles to internal dienes.