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Efficient 1,2-Addition of Aryl- and Alkenylboronic Acids to Aldehydes Catalyzed by the Palladium/Thioether−Imidazolinium Chloride System

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Masami Kuriyama,* Rumiko Shimazawa, and Ryuichi Shirai*

Faculty of Pharmaceutical Sciences, Doshisha Women's College of Liberal Arts, Kodo, Kyotanabe, Kyoto 610-0395, Japan mkuriyam@dwc.doshisha.ac.jp; rshirai@dwc.doshisha.ac.jp

J. Org. Chem., 2008, 73 (4), pp 1597–1600

DOI: 10.1021/jo7020983

Publication Date (Web): January 11, 2008

Section:

Benzene, Its Derivatives, and Condensed Benzenoid Compounds

Abstract

The high level of catalyst performance was attainable in the palladium-catalyzed 1,2-addition of aryl-, heteroaryl-, and alkenylboronic acids to aromatic, heteroaromatic, and aliphatic aldehydes using thioether−imidazolinium chloride L5 as a heterobidentate carbene ligand precursor.

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Citing Articles

View all 11 citing articles

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This article has been cited by 10 ACS Journal articles (5 most recent appear below).

Novel Heterotetranuclear V₂Mo₂ or V₂W₂ Complexes with 4,4′-Di-tert-butyl-2,2′-bipyridine: Syntheses, Crystal Structures, and Catalytic Activities
Shintaro Kodama, Akihiro Nomoto, Shigenobu Yano, Michio Ueshima, and Akiya Ogawa
Inorganic Chemistry2011 50 (20), 9942-9947
- Novel Heterotetranuclear V₂Mo₂ or V₂W₂ Complexes with 4,4′-Di-tert-butyl-2,2′-bipyridine: Syntheses, Crystal Structures, and Catalytic Activities
  Shintaro Kodama, Akihiro Nomoto, Shigenobu Yano, Michio Ueshima, and Akiya Ogawa
  Inorganic Chemistry2011 50 (20), 9942-9947
  Two novel heterotetranuclear complexes [V2O2(μ-MeO)2(μ-WO4)2(4,4′-tBubpy)2] (1) and [V2O2(μ-MeO)2(μ-MoO4)2(4,4′-tBubpy)2] (2) were synthesized, and the solid state structures of these complexes were revealed by single crystal X-ray crystallography. The ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Transmetalation of Unsaturated Carbon Nucleophiles from Boron-Containing Species to the Mid to Late d-Block Metals of Relevance to Catalytic C−X Coupling Reactions (X = C, F, N, O, Pb, S, Se, Te)
David V. Partyka
Chemical Reviews2011 111 (3), 1529-1595
- Transmetalation of Unsaturated Carbon Nucleophiles from Boron-Containing Species to the Mid to Late d-Block Metals of Relevance to Catalytic C−X Coupling Reactions (X = C, F, N, O, Pb, S, Se, Te)
  David V. Partyka
  Chemical Reviews2011 111 (3), 1529-1595
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Aryl Ketone Synthesis via Tandem Orthoplatinated Triarylphosphite-Catalyzed Addition Reactions of Arylboronic Acids with Aldehydes Followed by Oxidation
Yuan-Xi Liao and Qiao-Sheng Hu
The Journal of Organic Chemistry2010 75 (20), 6986-6989
- Aryl Ketone Synthesis via Tandem Orthoplatinated Triarylphosphite-Catalyzed Addition Reactions of Arylboronic Acids with Aldehydes Followed by Oxidation
  Yuan-Xi Liao and Qiao-Sheng Hu
  The Journal of Organic Chemistry2010 75 (20), 6986-6989
  Tandem orthoplatinated triaryl phosphite-catalyzed addition reactions of arylboronic acids with aldehydes followed by oxidation to yield aryl ketones is described. 3-Pentanone was identified as a suitable oxidant for the tandem aryl ketone formation ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Palladium-Catalyzed Cascade Aryl Addition/Intramolecular Lactonization of Phthalaldehyde To Access 3-Aryl- and Alkenylphthalides
Zhishi Ye, Pengcheng Qian, Guanglei Lv, Fang Luo and Jiang Cheng
The Journal of Organic Chemistry2010 75 (17), 6043-6045
- Palladium-Catalyzed Cascade Aryl Addition/Intramolecular Lactonization of Phthalaldehyde To Access 3-Aryl- and Alkenylphthalides
  Zhishi Ye, Pengcheng Qian, Guanglei Lv, Fang Luo and Jiang Cheng
  The Journal of Organic Chemistry2010 75 (17), 6043-6045
  A palladium-catalyzed addition of arylboronic acids to phthalaldehyde, followed by an intramolecular lactonization to access 3-substituted phthalides, is described. The procedure tolerates a series of functional groups, such as methoxyl, fluoro, chloro, ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Efficient Synthesis of 3-Arylphthalides using Palladium-Catalyzed Arylation of Aldehydes with Organoboronic Acids
Masami Kuriyama, Natsuki Ishiyama, Rumiko Shimazawa, Ryuichi Shirai and Osamu Onomura
The Journal of Organic Chemistry2009 74 (23), 9210-9213
- Efficient Synthesis of 3-Arylphthalides using Palladium-Catalyzed Arylation of Aldehydes with Organoboronic Acids
  Masami Kuriyama, Natsuki Ishiyama, Rumiko Shimazawa, Ryuichi Shirai and Osamu Onomura
  The Journal of Organic Chemistry2009 74 (23), 9210-9213
  The synthesis of 3-arylphthalides via palladium-catalyzed arylation of aldehydes with organoboronic acids was achieved using the thioether-imidazolinium carbene ligand in good to excellent yields and was carried out using 1.0 mol % of the catalyst with ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links

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Published In Issue February 15, 2008
Received September 26, 2007

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Note

Efficient 1,2-Addition of Aryl- and Alkenylboronic Acids to Aldehydes Catalyzed by the Palladium/Thioether−Imidazolinium Chloride System

Abstract

Citing Articles

Novel Heterotetranuclear V₂Mo₂ or V₂W₂ Complexes with 4,4′-Di-tert-butyl-2,2′-bipyridine: Syntheses, Crystal Structures, and Catalytic Activities

Novel Heterotetranuclear V₂Mo₂ or V₂W₂ Complexes with 4,4′-Di-tert-butyl-2,2′-bipyridine: Syntheses, Crystal Structures, and Catalytic Activities

Transmetalation of Unsaturated Carbon Nucleophiles from Boron-Containing Species to the Mid to Late d-Block Metals of Relevance to Catalytic C−X Coupling Reactions (X = C, F, N, O, Pb, S, Se, Te)

Transmetalation of Unsaturated Carbon Nucleophiles from Boron-Containing Species to the Mid to Late d-Block Metals of Relevance to Catalytic C−X Coupling Reactions (X = C, F, N, O, Pb, S, Se, Te)

Aryl Ketone Synthesis via Tandem Orthoplatinated Triarylphosphite-Catalyzed Addition Reactions of Arylboronic Acids with Aldehydes Followed by Oxidation

Aryl Ketone Synthesis via Tandem Orthoplatinated Triarylphosphite-Catalyzed Addition Reactions of Arylboronic Acids with Aldehydes Followed by Oxidation

Palladium-Catalyzed Cascade Aryl Addition/Intramolecular Lactonization of Phthalaldehyde To Access 3-Aryl- and Alkenylphthalides

Palladium-Catalyzed Cascade Aryl Addition/Intramolecular Lactonization of Phthalaldehyde To Access 3-Aryl- and Alkenylphthalides

Efficient Synthesis of 3-Arylphthalides using Palladium-Catalyzed Arylation of Aldehydes with Organoboronic Acids