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Literature DB >> 26129922

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

Nusrah Hussain¹, Byeong-Seon Kim¹, Patrick J Walsh².

Abstract

Diarylmethylamines are key intermediates and products in the pharmaceutical industry. Herein we disclose a novel method toward the synthesis of these important compounds via CH functionalization. Presented is a reversible deprotonation of N-Boc benzylalkylamines at the benzylic CH with in situ arylation by a NiXantPhos-based palladium catalyst (50-93 % yield, 29 examples). The method is also successful with N-Boc-tetrahydroisoquinolines. The advantages of this method are it avoids strong bases, low temperatures, and the need to transmetallate to main group metals for the coupling.

Entities: CellLine Chemical Disease Species

Keywords: CH functionalization; NiXantPhos ligand; cross-coupling; diarylmethylamines; pallladium

Mesh：

Substances：

Year: 2015 PMID： 26129922 PMCID： PMC5079650 DOI： 10.1002/chem.201502017

Source DB: PubMed Journal: Chemistry ISSN： 0947-6539 Impact factor: 5.236

40 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

2. Quantitative structure-activity relationship studies on 1-aryl-tetrahydroisoquinoline analogs as active anti-HIV agents.

Authors: Ke-xian Chen; Hai-ying Xie; Zu-guang Li; Jian-rong Gao
Journal: Bioorg Med Chem Lett Date: 2008-09-18 Impact factor: 2.823

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. CuBr-catalyzed direct indolation of tetrahydroisoquinolines via cross-dehydrogenative coupling between sp3 C-H and sp2 C-H bonds.

Authors: Zhiping Li; Chao-Jun Li
Journal: J Am Chem Soc Date: 2005-05-18 Impact factor: 15.419

5. Highly diastereoselective arylations of substituted piperidines.

Authors: Stephanie Seel; Tobias Thaler; Keishi Takatsu; Cong Zhang; Hendrik Zipse; Bernd F Straub; Peter Mayer; Paul Knochel
Journal: J Am Chem Soc Date: 2011-03-09 Impact factor: 15.419

6. Enantioselective, palladium-catalyzed alpha-arylation of N-Boc-pyrrolidine.

Authors: Kevin R Campos; Artis Klapars; Jacob H Waldman; Peter G Dormer; Cheng-yi Chen
Journal: J Am Chem Soc Date: 2006-03-22 Impact factor: 15.419

7. Mechanism of the Pd-catalyzed decarboxylative allylation of α-imino esters: decarboxylation via free carboxylate ion.

Authors: Zhe Li; Yuan-Ye Jiang; Andrew A Yeagley; James P Bour; Lei Liu; Jason J Chruma; Yao Fu
Journal: Chemistry Date: 2012-09-23 Impact factor: 5.236

8. Tandem C-C bond-forming processes: interception of the pd-catalyzed decarboxylative allylation of allyl diphenylglycinate imines with activated olefins.

Authors: Andrew A Yeagley; Melissa A Lowder; Jason J Chruma
Journal: Org Lett Date: 2009-09-03 Impact factor: 6.005

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

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

2. Quantitative structure-activity relationship studies on 1-aryl-tetrahydroisoquinoline analogs as active anti-HIV agents.

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

4. CuBr-catalyzed direct indolation of tetrahydroisoquinolines via cross-dehydrogenative coupling between sp3 C-H and sp2 C-H bonds.

5. Highly diastereoselective arylations of substituted piperidines.

6. Enantioselective, palladium-catalyzed alpha-arylation of N-Boc-pyrrolidine.

7. Mechanism of the Pd-catalyzed decarboxylative allylation of α-imino esters: decarboxylation via free carboxylate ion.

8. Tandem C-C bond-forming processes: interception of the pd-catalyzed decarboxylative allylation of allyl diphenylglycinate imines with activated olefins.

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

10. Ligand-controlled asymmetric arylation of aliphatic α-amino anion equivalents.

1. Palladium-Catalyzed α-Arylation of Methyl Sulfonamides with Aryl Chlorides.

2. Synthesis of Diarylated 4-Pyridylmethyl Ethers via Palladium-Catalyzed Cross-Coupling Reactions.

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

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