Prev. Article Next Article Table of Contents

Note

Cationic Pd(II)/Bipyridine-Catalyzed Addition of Arylboronic Acids to Arylaldehydes. One-Pot Synthesis of Unsymmetrical Triarylmethanes

Your current credentials do not allow retrieval of the full text.

Purchase the full-text

PDF/HTML,
figures/images,
references and tables,
(where available)

Shaohui Lin and Xiyan Lu*

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China xylu@mail.sioc.ac.cn

J. Org. Chem., 2007, 72 (25), pp 9757–9760

DOI: 10.1021/jo071232k

Publication Date (Web): November 14, 2007

Section:

Benzene, Its Derivatives, and Condensed Benzenoid Compounds

Abstract

Cationic Pd(II) complex-catalyzed addition of arylboronic acids to aldehydes with low catalyst loading was developed with high yields. One-pot synthesis of unsymmetrical triarylmethanes from arylboronic acids, aryl aldehydes, and electron-rich arenes was achieved in high yields.

View: Full Text HTML | Hi-Res PDF | PDF w/ Links

Citing Articles

View all 39 citing articles

Citation data is made available by participants in CrossRef's Cited-by Linking service. For a more comprehensive list of citations to this article, users are encouraged to perform a search in SciFinder.

This article has been cited by 12 ACS Journal articles (5 most recent appear below).

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
Cationic Pd(II)-Catalyzed Tandem Reaction of 2-Arylethynylanilines and Aldehydes: An Efficient Synthesis of Substituted 3-Hydroxymethyl Indoles
Xiuling Han and Xiyan Lu
Organic Letters2010 12 (15), 3336-3339
- Cationic Pd(II)-Catalyzed Tandem Reaction of 2-Arylethynylanilines and Aldehydes: An Efficient Synthesis of Substituted 3-Hydroxymethyl Indoles
  Xiuling Han and Xiyan Lu
  Organic Letters2010 12 (15), 3336-3339
  An efficient cationic palladium(II)-catalyzed synthesis of substituted 3-hydroxymethylindoles from readily accessible starting materials is developed. This tandem reaction involves an intramolecular aminopalladation of an alkyne and an addition to the ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Cationic Pd(II)/Bipyridine-Catalyzed Conjugate Addition of Arylboronic Acids to β,β-Disubstituted Enones: Construction of Quaternary Carbon Centers
Shaohui Lin and Xiyan Lu
Organic Letters2010 12 (11), 2536-2539
- Cationic Pd(II)/Bipyridine-Catalyzed Conjugate Addition of Arylboronic Acids to β,β-Disubstituted Enones: Construction of Quaternary Carbon Centers
  Shaohui Lin and Xiyan Lu
  Organic Letters2010 12 (11), 2536-2539
  Cationic Pd(II)-catalyzed addition of arylboronic acids to β,β-disubstituted enones in high yields was developed. This method provided an efficient method for the construction of quaternary carbon centers, and only 0.5 mol % of Pd(II) catalyst was ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links

Tools

SciFinder Links

Explore by:

Author of this Article Any Author Research Topic

History

Published In Issue December 07, 2007
Received June 20, 2007

Select a CAS section from the 5 main topical divisions below:

Note

Cationic Pd(II)/Bipyridine-Catalyzed Addition of Arylboronic Acids to Arylaldehydes. One-Pot Synthesis of Unsymmetrical Triarylmethanes

Abstract

Citing Articles

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

Cationic Pd(II)-Catalyzed Tandem Reaction of 2-Arylethynylanilines and Aldehydes: An Efficient Synthesis of Substituted 3-Hydroxymethyl Indoles

Cationic Pd(II)-Catalyzed Tandem Reaction of 2-Arylethynylanilines and Aldehydes: An Efficient Synthesis of Substituted 3-Hydroxymethyl Indoles

Cationic Pd(II)/Bipyridine-Catalyzed Conjugate Addition of Arylboronic Acids to β,β-Disubstituted Enones: Construction of Quaternary Carbon Centers

Cationic Pd(II)/Bipyridine-Catalyzed Conjugate Addition of Arylboronic Acids to β,β-Disubstituted Enones: Construction of Quaternary Carbon Centers

Tools

SciFinder Links

History

Recommend & Share

Related Content

Palladium-Catalyzed Addition of Arylboronic Acids to Aldehydes

The Palladium-Catalyzed Addition of Aryl- and Heteroarylboronic Acids to Aldehydes

Cationic Palladium Complex Catalyzed Highly Enantioselective Intramolecular Addition of Arylboronic Acids to Ketones. A Convenient Synthesis of Optically Active Cycloalkanols

Other ACS content by these authors:

JOURNALS

BOOKS

C&EN

TOOLS

COMMUNITIES

DIRECTORIES & DATABASES

LEGACY MAGAZINES

Products

User Resources

Support

Partners

Search ACS Publications