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Literature DB >> 18947231

Carbonylative cross-coupling of ortho-disubstituted aryl iodides. convenient synthesis of sterically hindered aryl ketones.

B Michael O'Keefe¹, Nicholas Simmons, Stephen F Martin.

Abstract

A mild and general protocol for the carbonylative cross-coupling of sterically hindered ortho-disubstituted aryl iodides is reported. Carbonylative Suzuki-Miyaura couplings of a variety of aryl boronic acids provide an array of substituted biaryl ketones in modest to excellent yield. A carbonylative Negishi coupling that utilizes alkynyl nucleophiles is also described.

Entities: Chemical Disease Species

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Year: 2008 PMID： 18947231 PMCID： PMC2636973 DOI： 10.1021/ol802202j

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

16 in total

1. Synthesis and protein kinase inhibitory activity of balanol analogues with modified benzophenone subunits.

Authors: John W Lampe; Christopher K Biggers; Jean M Defauw; Robert J Foglesong; Steven E Hall; Julia M Heerding; Sean P Hollinshead; Hong Hu; Philip F Hughes; G Erik Jagdmann; Mary George Johnson; Yen-Shi Lai; Christopher T Lowden; Michael P Lynch; José S Mendoza; Marcia M Murphy; Joseph W Wilson; Lawrence M Ballas; Kiyomi Carter; James W Darges; Jefferson E Davis; Frederick R Hubbard; Mark L Stamper
Journal: J Med Chem Date: 2002-06-06 Impact factor: 7.446

2. Benzophenone C-glucosides from Polygala telephioides.

Authors: J C Li; T Nohara
Journal: Chem Pharm Bull (Tokyo) Date: 2000-09 Impact factor: 1.645

3. Four new phenones from the cortexes of Polygala tenuifolia.

Authors: Yong Jiang; Pengfei Tu
Journal: Chem Pharm Bull (Tokyo) Date: 2005-09 Impact factor: 1.645

Review 4. Palladium complexes of N-heterocyclic carbenes as catalysts for cross-coupling reactions--a synthetic chemist's perspective.

Authors: Eric Assen B Kantchev; Christopher J O'Brien; Michael G Organ
Journal: Angew Chem Int Ed Engl Date: 2007 Impact factor: 15.336

5. Catalysts for Suzuki-Miyaura coupling processes: scope and studies of the effect of ligand structure.

Authors: Timothy E Barder; Shawn D Walker; Joseph R Martinelli; Stephen L Buchwald
Journal: J Am Chem Soc Date: 2005-04-06 Impact factor: 15.419

6. A user-friendly, all-purpose Pd-NHC (NHC=N-heterocyclic carbene) precatalyst for the negishi reaction: a step towards a universal cross-coupling catalyst.

Authors: Michael G Organ; Stephanie Avola; Igor Dubovyk; Niloufar Hadei; Eric Assen B Kantchev; Christopher J O'Brien; Cory Valente
Journal: Chemistry Date: 2006-06-14 Impact factor: 5.236

7. Natural and synthetic benzophenones: interaction with the cytosolic binding domain of P-glycoprotein.

Authors: S Rancon; A Chaboud; N Darbour; G Comte; C Bayet; P N Simon; J Raynaud; A Di Pietro; P Cabalion; D Barron
Journal: Phytochemistry Date: 2001-06 Impact factor: 4.072

8. Carbonylative Sonogashira coupling of terminal alkynes with aqueous ammonia.

Authors: Mohamed S Mohammed Ahmed; Atsunori Mori
Journal: Org Lett Date: 2003-08-21 Impact factor: 6.005

9. N-heterocyclic carbenes: a new concept in organometallic catalysis.

Authors: Wolfgang A Herrmann
Journal: Angew Chem Int Ed Engl Date: 2002-04-15 Impact factor: 15.336

10. Synthesis of S-acetyl oligoarylenedithiols via Suzuki-Miyaura cross-coupling.

Authors: Alessandra Operamolla; Omar Hassan Omar; Francesco Babudri; Gianluca M Farinola; Francesco Naso
Journal: J Org Chem Date: 2007-11-29 Impact factor: 4.354

9 in total

1. Studies Toward the Syntheses of Pluramycin Natural Products. The First Total Synthesis of Isokidamycin.

Authors: B Michael O'Keefe; Douglas M Mans; David E Kaelin; Stephen F Martin
Journal: Tetrahedron Date: 2011-09-02 Impact factor: 2.457

2. Facile Access to Sterically Hindered Aryl Ketones via Carbonylative Cross-Coupling: Application to the Total Synthesis of Luteolin.

Authors: B Michael O'Keefe; Nicholas Simmons; Stephen F Martin
Journal: Tetrahedron Date: 2011-06-17 Impact factor: 2.457

Carbonylative cross-coupling of ortho-disubstituted aryl iodides. convenient synthesis of sterically hindered aryl ketones.

1. Synthesis and protein kinase inhibitory activity of balanol analogues with modified benzophenone subunits.

2. Benzophenone C-glucosides from Polygala telephioides.

3. Four new phenones from the cortexes of Polygala tenuifolia.

Review 4. Palladium complexes of N-heterocyclic carbenes as catalysts for cross-coupling reactions--a synthetic chemist's perspective.

5. Catalysts for Suzuki-Miyaura coupling processes: scope and studies of the effect of ligand structure.

6. A user-friendly, all-purpose Pd-NHC (NHC=N-heterocyclic carbene) precatalyst for the negishi reaction: a step towards a universal cross-coupling catalyst.

7. Natural and synthetic benzophenones: interaction with the cytosolic binding domain of P-glycoprotein.

8. Carbonylative Sonogashira coupling of terminal alkynes with aqueous ammonia.

9. N-heterocyclic carbenes: a new concept in organometallic catalysis.

10. Synthesis of S-acetyl oligoarylenedithiols via Suzuki-Miyaura cross-coupling.

1. Studies Toward the Syntheses of Pluramycin Natural Products. The First Total Synthesis of Isokidamycin.

2. Facile Access to Sterically Hindered Aryl Ketones via Carbonylative Cross-Coupling: Application to the Total Synthesis of Luteolin.

3. Natural Products and Their Mimics as Targets of Opportunity for Discovery.

4. Enantioselective total synthesis of (-)-citrinadin A and revision of its stereochemical structure.

5. Reversed-Polarity Synthesis of Diaryl Ketones through Palladium-Catalyzed Direct Arylation of 2-Aryl-1,3-dithianes.

6. Total synthesis of isokidamycin.

7. Chemical and biological studies of nakiterpiosin and nakiterpiosinone.

8. Palladium-Catalyzed Hydroxycarbonylation of (Hetero)aryl Halides for DNA-Encoded Chemical Library Synthesis.

9. Enantioselective total syntheses of citrinadins A and B. Stereochemical revision of their assigned structures.