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Literature DB >> 26576005

Palladium-Catalyzed Benzylic C-H Arylation of Azaarylmethylamines.

Byeong-Seon Kim¹, Jacqueline Jiménez^1,2, Feng Gao^1,3, Patrick J Walsh¹.

Abstract

A direct C-H functionalization approach to produce aryl(azaaryl)methylamines from azaarylmethylamines without directing groups is described. Under conditions where the azaarylmethylamines' C-H is reversibly deprotonated, a Pd(OAc)(2)/NIXANTPHOS-based catalyst couples the resulting carbanions with various aryl halides to provide aryl(azaaryl)methylamines. This umpolung strategy directly provides tertiary amines without protecting or activating groups.

Entities: CellLine Chemical Disease Species

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Year: 2015 PMID： 26576005 PMCID： PMC4880366 DOI： 10.1021/acs.orglett.5b02898

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

45 in total

1. Synthesis of diarylmethylamines via palladium-catalyzed regioselective arylation of 1,1,3-triaryl-2-azaallyl anions.

Authors: Minyan Li; Baris Yücel; Javier Adrio; Ana Bellomo; Patrick J Walsh
Journal: Chem Sci Date: 2014-06-01 Impact factor: 9.825

Review 2. Quinoline, quinazoline and acridone alkaloids.

Authors: Joseph P Michael
Journal: Nat Prod Rep Date: 2005-08-24 Impact factor: 13.423

3. 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

4. Ligand-controlled α- and β-arylation of acyclic N-Boc amines.

Authors: Anthony Millet; David Dailler; Paolo Larini; Olivier Baudoin
Journal: Angew Chem Int Ed Engl Date: 2014-02-06 Impact factor: 15.336

5. 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

6. 4,5-dihydroxypyrimidine carboxamides and N-alkyl-5-hydroxypyrimidinone carboxamides are potent, selective HIV integrase inhibitors with good pharmacokinetic profiles in preclinical species.

Authors: Vincenzo Summa; Alessia Petrocchi; Victor G Matassa; Cristina Gardelli; Ester Muraglia; Michael Rowley; Odalys Gonzalez Paz; Ralph Laufer; Edith Monteagudo; Paola Pace
Journal: J Med Chem Date: 2006-11-16 Impact factor: 7.446

6. Regio- and chemoselective Csp³-H arylation of benzylamines by single electron transfer/hydrogen atom transfer synergistic catalysis.

Authors: Takafumi Ide; Joshua P Barham; Masashi Fujita; Yuji Kawato; Hiromichi Egami; Yoshitaka Hamashima
Journal: Chem Sci Date: 2018-09-12 Impact factor: 9.825

6 in total

Palladium-Catalyzed Benzylic C-H Arylation of Azaarylmethylamines.

1. Synthesis of diarylmethylamines via palladium-catalyzed regioselective arylation of 1,1,3-triaryl-2-azaallyl anions.

Review 2. Quinoline, quinazoline and acridone alkaloids.

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

4. Ligand-controlled α- and β-arylation of acyclic N-Boc amines.

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

6. 4,5-dihydroxypyrimidine carboxamides and N-alkyl-5-hydroxypyrimidinone carboxamides are potent, selective HIV integrase inhibitors with good pharmacokinetic profiles in preclinical species.

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

Review 8. An overview of the synthetic routes to the best selling drugs containing 6-membered heterocycles.

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

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

1. Palladium-Catalyzed Selective α-Alkenylation of Pyridylmethyl Ethers with Vinyl Bromides.

2. Palladium-Catalyzed Triarylation of sp³ C-H Bonds in Heteroarylmethanes: Synthesis of Triaryl(heteroaryl)methanes.

3. Arylation of Azaarylmethylamines with Aryl Chlorides and a NiBr₂/NIXANTPHOS-based Catalyst.

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

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

6. Regio- and chemoselective Csp³-H arylation of benzylamines by single electron transfer/hydrogen atom transfer synergistic catalysis.