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Literature DB >> 24295336

Palladium-catalyzed α-arylation of benzylic phosphine oxides.

Sonia Montel¹, Tiezheng Jia, Patrick J Walsh.

Abstract

A novel approach to prepare diarylmethyl phosphine oxides from benzyl phosphine oxides via deprotonative cross-coupling processes (DCCP) is reported. The optimization of the reaction was guided by High-Throughput Experimentation (HTE) techniques. The Pd(OAc)2/Xantphos-based catalyst enabled the reaction between benzyl diphenyl or dicyclohexyl phosphine oxide derivatives and aryl bromides in good to excellent yields (51-91%).

Entities: Chemical Disease Gene

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Year: 2013 PMID： 24295336 PMCID： PMC3913533 DOI： 10.1021/ol403124g

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

25 in total

1. Highly active, air-stable versatile palladium catalysts for the C-C, C-N, and C-S bond formations via cross-coupling reactions of aryl chlorides.

Authors: G Y Li; G Zheng; A F Noonan
Journal: J Org Chem Date: 2001-12-14 Impact factor: 4.354

2. Synthesis of α-Arylphosphonates Using Copper-Catalyzed α-Arylation and Deacylative α-Arylation of β-Ketophosphonates.

Authors: Laxmidhar Rout; Sridhar Regati; Cong-Gui Zhao
Journal: Adv Synth Catal Date: 2011-12-06 Impact factor: 5.837

3. Ruthenium-catalyzed formation of aryl(diphenyl)phosphine oxides by reactions of propargylic alcohols with diphenylphosphine oxide.

Authors: Gen Onodera; Hideyuki Matsumoto; Marilyn Daisy Milton; Yoshiaki Nishibayashi; Sakae Uemura
Journal: Org Lett Date: 2005-09-01 Impact factor: 6.005

4. Efficient aryl-(hetero)aryl coupling by activation of C-Cl and C-F bonds using nickel complexes of air-stable phosphine oxides.

Authors: Lutz Ackermann; Robert Born; Julia H Spatz; Daniel Meyer
Journal: Angew Chem Int Ed Engl Date: 2005-11-11 Impact factor: 15.336

5. Heteroscorpionate rare-earth metal zwitterionic complexes: syntheses, characterization, and heteroselective catalysis on the ring-opening polymerization of rac-lactide.

Authors: Zhichao Zhang; Dongmei Cui
Journal: Chemistry Date: 2011-08-31 Impact factor: 5.236

6. Palladium-catalyzed C(sp3)-H arylation of diarylmethanes at room temperature: synthesis of triarylmethanes via deprotonative-cross-coupling processes.

Authors: Jiadi Zhang; Ana Bellomo; Andrea D Creamer; Spencer D Dreher; Patrick J Walsh
Journal: J Am Chem Soc Date: 2012-08-07 Impact factor: 15.419

7. Palladium-catalyzed direct arylation of methyl sulfoxides with aryl halides.

Authors: Tiezheng Jia; Ana Bellomo; Kawtar E L Baina; Spencer D Dreher; Patrick J Walsh
Journal: J Am Chem Soc Date: 2013-02-27 Impact factor: 15.419

8. Palladium-catalyzed direct intermolecular α-arylation of amides with aryl chlorides.

Authors: Bing Zheng; Tiezheng Jia; Patrick J Walsh
Journal: Org Lett Date: 2013-08-05 Impact factor: 6.005

9. Palladium catalyzed cross-coupling reactions for phosphorus-carbon bond formation.

Authors: Adrian L Schwan
Journal: Chem Soc Rev Date: 2004-03-10 Impact factor: 54.564

10. The preparation of 2,6-disubstituted pyridinyl phosphine oxides as novel anti-cancer agents.

Authors: Kim Hung Lam; Roberto Gambari; Marcus Chun Wah Yuen; Chi Wai Kan; Penni Chan; Lijin Xu; Weijun Tang; Chung Hin Chui; Gregory Yin Ming Cheng; Raymond Siu Ming Wong; Fung Yi Lau; Cindy Sze Wai Tong; Andrew Kit Wah Chan; Paul Bo San Lai; Stanton Hon Lung Kok; Chor Hing Cheng; Albert Sun Chi Chan; Johnny Cheuk On Tang
Journal: Bioorg Med Chem Lett Date: 2009-02-27 Impact factor: 2.823

14 in total

Palladium-catalyzed α-arylation of benzylic phosphine oxides.

1. Highly active, air-stable versatile palladium catalysts for the C-C, C-N, and C-S bond formations via cross-coupling reactions of aryl chlorides.

2. Synthesis of α-Arylphosphonates Using Copper-Catalyzed α-Arylation and Deacylative α-Arylation of β-Ketophosphonates.

3. Ruthenium-catalyzed formation of aryl(diphenyl)phosphine oxides by reactions of propargylic alcohols with diphenylphosphine oxide.

4. Efficient aryl-(hetero)aryl coupling by activation of C-Cl and C-F bonds using nickel complexes of air-stable phosphine oxides.

5. Heteroscorpionate rare-earth metal zwitterionic complexes: syntheses, characterization, and heteroselective catalysis on the ring-opening polymerization of rac-lactide.

6. Palladium-catalyzed C(sp3)-H arylation of diarylmethanes at room temperature: synthesis of triarylmethanes via deprotonative-cross-coupling processes.

7. Palladium-catalyzed direct arylation of methyl sulfoxides with aryl halides.

8. Palladium-catalyzed direct intermolecular α-arylation of amides with aryl chlorides.

9. Palladium catalyzed cross-coupling reactions for phosphorus-carbon bond formation.

10. The preparation of 2,6-disubstituted pyridinyl phosphine oxides as novel anti-cancer agents.

1. Palladium-catalyzed C(sp(3))-H Arylation of N-Boc benzylalkylamines via a deprotonative cross-coupling process.

2. Tandem C(sp³)-H Arylation/Oxidation and Arylation/Allylic Substitution of Isoindolinones.

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

4. Palladium-Catalyzed Benzylic C-H Arylation of Azaarylmethylamines.

5. Palladium-Catalyzed Benzylic Arylation of Pyridylmethyl Silyl Ethers: One-Pot Synthesis of Aryl(pyridyl)methanols.

6. Room-temperature palladium-catalyzed direct 2-arylation of benzoxazoles with aryl and heteroaryl bromides.

7. Synthesis of triarylmethanols via tandem arylation/oxidation of diarylmethanes.

8. Chemoselective Palladium-Catalyzed Deprotonative Arylation/[1,2]-Wittig Rearrangement of Pyridylmethyl Ethers.

9. Palladium-catalyzed α-arylation of benzylic phosphonates.

10. NiXantphos: a deprotonatable ligand for room-temperature palladium-catalyzed cross-couplings of aryl chlorides.