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Literature DB >> 24765060

A General and Practical Palladium-Catalyzed Direct α-Arylation of Amides with Aryl Halides.

Bing Zheng¹, Tiezheng Jia², Patrick J Walsh².

Abstract

An efficient system for the direct catalytic intermolecular α-arylation of acetamide derivatives with aryl bromides and chlorides is presented. The palladium catalyst is supported by Kwong's indole-based phosphine ligand and provides monoarylated amides in up to 95% yield. Excellent chemoselectivities (>10:1) in the mono- and diarylation with aryl bromides were achieved by careful selection of bases, solvents, and stoichiometry. Under the coupling conditions, the weakly acidic α-protons of amides (pKa up to 35) were reversibly depotonated by LiO t Bu, NaO t Bu, or NaN(SiMe3)2.

Entities: Chemical Disease Gene

Keywords: C-C bond formation; amides; aryl halides; chemoselectivity; cross-coupling; palladium

Year: 2014 PMID： 24765060 PMCID： PMC3994175 DOI： 10.1002/adsc.201300851

Source DB: PubMed Journal: Adv Synth Catal ISSN： 1615-4150 Impact factor: 5.837

106 in total

1. Fischer indole synthesis with organozinc reagents.

Authors: Benjamin A Haag; Zhi-Guang Zhang; Jin-Shan Li; Paul Knochel
Journal: Angew Chem Int Ed Engl Date: 2010-12-03 Impact factor: 15.336

Review 2. Sigma-chelation-directed C-H functionalizations using Pd(II) and Cu(II) catalysts: regioselectivity, stereoselectivity and catalytic turnover.

Authors: Jin-Quan Yu; Ramesh Giri; Xiao Chen
Journal: Org Biomol Chem Date: 2006-11-21 Impact factor: 3.876

Review 3. Large-scale applications of transition metal-catalyzed couplings for the synthesis of pharmaceuticals.

Authors: Javier Magano; Joshua R Dunetz
Journal: Chem Rev Date: 2011-03-09 Impact factor: 60.622

4. 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

5. Tosylhydrazones: new uses for classic reagents in palladium-catalyzed cross-coupling and metal-free reactions.

Authors: José Barluenga; Carlos Valdés
Journal: Angew Chem Int Ed Engl Date: 2011-07-11 Impact factor: 15.336

6. Cross-coupling of C(sp)-H Bonds with Organometallic Reagents via Pd(II)/Pd(0) Catalysis**

Authors: Masayuki Wasa; Keary M Engle; Jin-Quan Yu
Journal: Isr J Chem Date: 2010-12 Impact factor: 3.333

7. Palladium-catalyzed intermolecular alpha-arylation of N-protected 2-piperidinones.

Authors: Janine Cossy; Arnault De Filippis; Domingo Gomez Pardo
Journal: Org Lett Date: 2003-08-21 Impact factor: 6.005

8. Palladium-catalyzed enantioselective alpha-arylation and alpha-vinylation of oxindoles facilitated by an axially chiral P-stereogenic ligand.

Authors: Alexander M Taylor; Ryan A Altman; Stephen L Buchwald
Journal: J Am Chem Soc Date: 2009-07-29 Impact factor: 15.419

9. Palladium-catalyzed alpha-arylation of oxindoles.

Authors: Matthew J Durbin; Michael C Willis
Journal: Org Lett Date: 2008-03-06 Impact factor: 6.005

10. An experimental and computational approach to defining structure/reactivity relationships for intramolecular addition reactions to bicyclic epoxonium ions.

Authors: Shuangyi Wan; Hakan Gunaydin; K N Houk; Paul E Floreancig
Journal: J Am Chem Soc Date: 2007-06-05 Impact factor: 15.419

14 in total

A General and Practical Palladium-Catalyzed Direct α-Arylation of Amides with Aryl Halides.

1. Fischer indole synthesis with organozinc reagents.

Review 2. Sigma-chelation-directed C-H functionalizations using Pd(II) and Cu(II) catalysts: regioselectivity, stereoselectivity and catalytic turnover.

Review 3. Large-scale applications of transition metal-catalyzed couplings for the synthesis of pharmaceuticals.

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

5. Tosylhydrazones: new uses for classic reagents in palladium-catalyzed cross-coupling and metal-free reactions.

6. Cross-coupling of C(sp)-H Bonds with Organometallic Reagents via Pd(II)/Pd(0) Catalysis**

7. Palladium-catalyzed intermolecular alpha-arylation of N-protected 2-piperidinones.

8. Palladium-catalyzed enantioselective alpha-arylation and alpha-vinylation of oxindoles facilitated by an axially chiral P-stereogenic ligand.

9. Palladium-catalyzed alpha-arylation of oxindoles.

10. An experimental and computational approach to defining structure/reactivity relationships for intramolecular addition reactions to bicyclic epoxonium ions.

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

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

8. Synthesis of (diarylmethyl)amines using Ni-catalyzed arylation of C(sp³)-H bonds.

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

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