[RuCl2(p-cymene)]2-Catalyzed Conjugate Addition of Arylboronic Acids to α,β-Unsaturated Ketones under Ligand-Free and Neutral Conditions

Lei Zhang; Xiaomin Xie; Lei Fu; Zhaoguo Zhang

doi:10.1021/jo4001367

[RuCl2(p-cymene)]2-Catalyzed Conjugate Addition of Arylboronic Acids to α,β-Unsaturated Ketones under Ligand-Free and Neutral Conditions

The Journal of Organic Chemistry ◽

10.1021/jo4001367 ◽

2013 ◽

Vol 78 (7) ◽

pp. 3434-3437 ◽

Cited By ~ 11

Author(s):

Lei Zhang ◽

Xiaomin Xie ◽

Lei Fu ◽

Zhaoguo Zhang

Keyword(s):

Conjugate Addition ◽

Unsaturated Ketones ◽

Arylboronic Acids ◽

Ligand Free ◽

Neutral Conditions

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ChemInform Abstract: [RuCl2(p-Cymene)]2-Catalyzed Conjugate Addition of Arylboronic Acids to α,β-Unsaturated Ketones under Ligand-Free and Neutral Conditions.

ChemInform ◽

10.1002/chin.201333067 ◽

2013 ◽

Vol 44 (33) ◽

pp. no-no

Author(s):

Lei Zhang ◽

Xiaomin Xie ◽

Lei Fu ◽

Zhaoguo Zhang

Keyword(s):

Conjugate Addition ◽

Unsaturated Ketones ◽

Arylboronic Acids ◽

Ligand Free ◽

Neutral Conditions

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ChemInform Abstract: Well-Defined [Rh(NHC)(OH)] Complexes Enabling the Conjugate Addition of Arylboronic Acids to α,β-Unsaturated Ketones.

ChemInform ◽

10.1002/chin.201212082 ◽

2012 ◽

Vol 43 (12) ◽

pp. no-no

Author(s):

Byron J. Truscott ◽

George C. Fortman ◽

Alexandra M. Z. Slawin ◽

Steven P. Nolan

Keyword(s):

Conjugate Addition ◽

Unsaturated Ketones ◽

Arylboronic Acids

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Well-defined [Rh(NHC)(OH)] complexes enabling the conjugate addition of arylboronic acids to α,β-unsaturated ketones

Organic & Biomolecular Chemistry ◽

10.1039/c1ob06112g ◽

2011 ◽

Vol 9 (20) ◽

pp. 7038 ◽

Cited By ~ 33

Author(s):

Byron J. Truscott ◽

George C. Fortman ◽

Alexandra M. Z. Slawin ◽

Steven P. Nolan

Keyword(s):

Conjugate Addition ◽

Unsaturated Ketones ◽

Arylboronic Acids

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ChemInform Abstract: Synthetic Approach to Flavanones and Flavones via Ligand-Free Palladium(II)-Catalyzed Conjugate Addition of Arylboronic Acids to Chromones.

ChemInform ◽

10.1002/chin.201308137 ◽

2013 ◽

Vol 44 (8) ◽

pp. no-no

Author(s):

Donghee Kim ◽

Kyungrok Ham ◽

Sungwoo Hong

Keyword(s):

Conjugate Addition ◽

Synthetic Approach ◽

Arylboronic Acids ◽

Ligand Free

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Bipyridyl-Based Diphosphine as an Efficient Ligand in the Rhodium-Catalyzed Asymmetric Conjugate Addition of Arylboronic Acids to α,β-Unsaturated Ketones.

ChemInform ◽

10.1002/chin.200348036 ◽

2003 ◽

Vol 34 (48) ◽

Author(s):

Qian Shi ◽

Lijin Xu ◽

Xingshu Li ◽

Xian Jia ◽

Ruihu Wang ◽

...

Keyword(s):

Conjugate Addition ◽

Unsaturated Ketones ◽

Arylboronic Acids

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A New Catalytic Activity of Antimony(III) Chloride in Palladium(0)-Catalyzed Conjugate Addition of Aromatics to .alpha.,.beta.-Unsaturated Ketones and Aldehydes with Sodium Tetraphenylborate and Arylboronic Acids

The Journal of Organic Chemistry ◽

10.1021/jo00109a019 ◽

1995 ◽

Vol 60 (4) ◽

pp. 883-888 ◽

Cited By ~ 88

Author(s):

Chan Sik Cho ◽

Shin-ichi Motofusa ◽

Kouichi Ohe ◽

Sakae Uemura ◽

Sang Chul Shim

Keyword(s):

Catalytic Activity ◽

Conjugate Addition ◽

Sodium Tetraphenylborate ◽

Unsaturated Ketones ◽

Arylboronic Acids ◽

Alpha Beta

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Bipyridyl-based diphosphine as an efficient ligand in the rhodium-catalyzed asymmetric conjugate addition of arylboronic acids to α,β-unsaturated ketones

Tetrahedron Letters ◽

10.1016/s0040-4039(03)01592-2 ◽

2003 ◽

Vol 44 (34) ◽

pp. 6505-6508 ◽

Cited By ~ 50

Author(s):

Qian Shi ◽

Lijin Xu ◽

Xingshu Li ◽

Xian Jia ◽

Ruihu Wang ◽

...

Keyword(s):

Conjugate Addition ◽

Unsaturated Ketones ◽

Arylboronic Acids

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ChemInform Abstract: A New Catalytic Activity of Antimony(III) Chloride in Palladium(0)- Catalyzed Conjugate Addition of Aromatics to α,β- Unsaturated Ketones and Aldehydes with Sodium Tetraphenylborate and Arylboronic Acids.

ChemInform ◽

10.1002/chin.199532098 ◽

2010 ◽

Vol 26 (32) ◽

pp. no-no

Author(s):

C. S. CHO ◽

S. MOTOFUSA ◽

K. OHE ◽

S. UEMURA ◽

S. C. SHIM

Keyword(s):

Catalytic Activity ◽

Conjugate Addition ◽

Sodium Tetraphenylborate ◽

Unsaturated Ketones ◽

Arylboronic Acids

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Synthetic approach to flavanones and flavones via ligand-free palladium(ii)-catalyzed conjugate addition of arylboronic acids to chromones

Organic & Biomolecular Chemistry ◽

10.1039/c2ob26061a ◽

2012 ◽

Vol 10 (36) ◽

pp. 7305 ◽

Cited By ~ 35

Author(s):

Donghee Kim ◽

Kyungrok Ham ◽

Sungwoo Hong

Keyword(s):

Conjugate Addition ◽

Synthetic Approach ◽

Arylboronic Acids ◽

Ligand Free

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Pd-catalysed conjugate addition of arylboronic acids to α,β-unsaturated ketones under microwave irradiation

Chemical Papers ◽

10.2478/s11696-011-0016-3 ◽

2011 ◽

Vol 65 (3) ◽

Cited By ~ 3

Author(s):

Viera Poláčková ◽

Vladimír Bariak ◽

Radovan Šebesta ◽

Štefan Toma

Keyword(s):

Acetic Acid ◽

Reaction Time ◽

Microwave Irradiation ◽

Conjugate Addition ◽

Cyclic Ketones ◽

Unsaturated Ketones ◽

Arylboronic Acids ◽

Cyclic Enones

AbstractThe Pd-catalysed conjugate addition of arylboronic acids to α,β-unsaturated cyclic ketones was studied under controlled microwave irradiation conditions. A variety of catalysts, bases and solvents was explored in order to achieve optimum yields in the shortest possible reaction time. Under optimised conditions (Pd(OAc)2/2,2′-bipyridine and KF in a mixture of toluene, water, and acetic acid and 10 min microwave irradiation), a range of arylboronic acids was successfully added to several cyclic enones. With chiral phosphane ligands, a promising enantioselectivity was obtained (85 % ee).

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