Catalytic Arylation Methods

Transcription

1 Anthony J. Burke and Carolina Silva Marques Catalytic Arylation Methods From the Academic Lab to Industrial Processes WlLEYVCH VerlagGmbH & Co. KG a A

2 VII Contents Preface XV List ofabbreviations XVII 1 CrossCoupling Arylations: Precedents and Rapid Historical Review of the Field MetalCatalyzed CrossCouplings: From Its Origins to the Nobel Prize and Beyond Arylation: What Is So Special? Recent New Developments Arylations with the HeckMizoroki Reaction Arylations with the HeckMatsuda ReactionRecent Developments HiyamaHatanaka CrossCoupling Arylations with the Stille Reaction 48 Reaction Arylations with the SonogashiraHagihara Reaction Arylations with the SuzukiMiyaura Reaction TamaoKumadaCorriu Cross Coupling NegishiBaba CrossCoupling Beyond the Ullmann and SuzukiMiyaura Reactions, Other Newer Approaches to Functional Biaryl Synthesis: Pd, Fe, Co, and Other Metals With Palladium With Iron With Nickel With Cobalt Conclusions Selected Experiments from the Literature The HeckMizoroki Reaction Heterogeneous Catalytic Synthesis of ( )Butyl Cinnamate Using a Palladium Nanosphere Catalyst The Preparative Catalytic Synthesis of 5(pTrifluoromethylphenyl)2,3dihydrofuran in Continuous Flow The HeckMatsuda Reaction Catalytic Synthesis of ( )3(4Methoxyphenyl)acryIic acid Using Palladium Acetate in Water Catalytic Synthesis of 2PhenylLWIndene Using Copper Chloride Catalytic Synthesis of (E)Ethyl 3(4methoxyphenyl)acryIate Using Palladium Nanoparticles Supported on Agarose Hydrogel The HeckHiyama Reaction Catalytic Synthesis of /7Nitrobiphenyl: LigandFree Coupling Using Pd/C The Stille Reaction 87

3 VIII Contents The Cu Catalyzed Stille Reaction Synthesis of A/EthylN (phenyl/>tolylmethyl)benzamide The SonogashiraHagihara Reaction The CopperFree Catalytic Synthesis of Diphenylethyne SonogashiraHagihara CrossCoupling with Arenediazonium SaltsSynthesis of l(4methoxyphenyl)2phenylacetylene The SuzukiMiyaura Reaction Synthesis of 4(2,6Dimethylphenyl)3,5dimethylisoxazole Using PdPEPPSIIPENT Synthesis/7Phenylanisole via the SuzukiMiyaura Reaction with a FibreCat1034 Catalyst Tamao Kumada Corriu CrossCoupling Reaction Synthesis of 2(4Methoxyphenyl)pyridine NegishiBaba CrossCoupling Synthesis of 1Mesitylnaphthalene Biaryl Synthesis with the Hindered Aryllithium Reagent, 2,6Dimethoxyphenyllithium: Catalytic Synthesis of l,3dimethoxy2(lnaphthyl)benzene 89 References 89 2 Amine, Phenol, Alcohol, and Thiol Arylation Introduction PdCatalyzed Processes BuchwaldHartwigArylations(CArNR Bond Formation) Migita Thioether Synthesis (CAr SR Bond Formation) Arylether Synthesis (CArOR Bond Formation) A Phosphorous Arylations (CArP Bond Formation) A. 1 PdCatalyzed Phosphorous Arylations (CAr P Bond Formation) CuCatalyzed and Promoted Arylations: (CArN Bond Formation) Arylamines (CN Bond Formation) The Modified Ullmann Reaction (UllmannCondensationType Arylations) Use of Arylboronic Acids and Derivatives Instead of Arylhalides: ChanLamEvans Coupling and Other Variants Arylthioethers (CArS Bond Formation) Use of Arylhalides The ChanLamEvans Variant (Use of Arylboronic Acids) Arylethers (CAr O Bond Formation) The CopperCatalyzed Ullmann Coupling Reaction The ChanLamEvans Reaction A Phosphorous Arylations (CArP Bond Formation) FeCatalyzed Arylations FeCatalyzed Aryl Amination: (CAr N Bond Formation) Arylethers (CAr0 Bond Formation) 136 2A3 Arylthioethers (CAr 2.5 NiCatalyzed Reactions 137 S Bond Formation) NiCatalyzed Amine Arylation: (CArN Bond Formation) NiCatalyzed Sulfide Arylation: (CAr S Bond Formation) NiCatalyzed Phosphorous Arylations (CArP Bond Formation) CoCatalyzed Arylations CoCatalyzed Amine Arylations: (CArN Bond Formation) CoCatalyzed Sulfide Arylation: (CArS Bond Formation) MnCatalyzed Arylations 140

4 Contents IX MnCatalyzed Amine Arylations: (CArN Bond Formation) MnCatalyzed Sulfide Arylation: (CAr S Bond Formation) CdCatalyzed Arylations CdCatalyzed Aryl Amination: (CAr N Bond Formation) Bi(III) and Indium OxideCatalyzed Thiol Arylations Conclusions and Final Comment Selected Experiments from the Literature Amine Arylations The BuchwaldHartwig Amine Arylation CopperCatalyzed Amine Arylations Fe Arylations Thiol Arylation PalladiumCatalyzed Arylation CopperCatalyzed Thiol Arylation Fe Catalysis Etherification CrossCoupling Reactions With Palladium With Iron 145 References Decarboxyiative Coupling Techniques Introduction PdCatalyzed Versions PdBased Systems Pd/CuBased Systems Other MetalCatalyzed Versions CuBased Systems Other MetalBased Systems Conclusions Selected Experiments Application of Pd Catalysts Synthesis of 2(3Pyridyl)lmethylpyrrole Synthesis of lmethyl2,3bis(4(trifluoromethyi)phenyl)lttindole Synthesis of 2,6Dimethoxybiphenyl Synthesis of 7(Diethylamino)3(4methoxyphenyl)2//chromen2one Synthesis of 4(2Nitrophenyl)benzophenone Synthesis of 3,4'Dimethyl4nitrobiphenyl Synthesis of 4Methylbenzophenone Synthesis of N[(lNaphthyl)(phenyl)methylene]cyclohexanamine Synthesis of 2,3.4,5,6Pentafluoro2'methylbiphenyl 171 References CH Bond Activation for Arylations Introduction C(sp2)H Activations Involving Ar/Ar Couplings C(sp2)H Activations Directed Metalating Group (DMG)Assisted C(sp2)H Activations Direct Arylation Involving Ar/C=X (X = C, O, N) Couplings C(sp2)H Activations 194 = DMG Ar/C=X (X C, O, N) Couplings C(sp2)H Activations NonDMG Ar/C=X(X = CO, N) Couplings C(sp2)H Activations 216

5 X Contents Involving Ar/Alkyne Couplings C(sp2)H Activations DMG Ar/Alkyne Couplings C(sp2)H Activations NonDMG Ar/Alkyne Couplings C(sp2)H Activations Involving Ar/Alkyl Couplings DMG Assisted Ar/Alkyl Couplings C(sp2)H Activations NonDMG Assisted Ar/Alkyl Couplings C(sp2)H Activations Involving Ar/N Couplings C(sp2)H Activations Involving Ar/Other Heteroatom Couplings Conclusions Selected Experiments from the Literature CAr H Arylation With Palladium With Rhodium With Ruthenium CAr H C=X (X = C, O, N) CrossCoupling With Rhodium With Ruthenium CArH Alkyne CrossCouplings With Rhodium 243 References Conjugate Additions Conjugate Additions: A Powerful Tool for Appending Organic Residues to Cyclic and Acyclic Substrates Applications ofrh Catalysts Applications ofpd Catalysts Applications ofru and Other Catalysts Ruthenium Copper Nickel Conclusions Selected Experiments Application of Rh Catalysts Synthesis of (S)3Phenylcyclohexanone Synthesis of a Bidentate Phosphoramidite Ligand: AT,.WDimethyl (i?,i?)0linkedphosphoramidite Synthesis of (J?)3(2Naphthyl)cyclohexanone Application of Pd Catalysts Synthesis of ( )2(Biphenyl4yl)4oxopiperidinelcarboxylic acid iertbutyl Ester Application of Cu Catalysts Synthesis of (fl)(+)3ethyl3methylcyclohexanone 288 References Imine ArylationsSynthesisof Arylamines Arylation of C=N Bonds: Simple Access to Chiral Amine Units Application ofrh Catalysts Application of Pd Catalysts Application of Ru and Other Catalysts Ruthenium Zinc 314

6 Contents XI Copper The PetasisAkritopoulou 6.6 Conclusions Selected Experiments Application ofrh Catalysts 324 Reaction Synthesis of (5)A?[(2Furyl)phenylmethyl]4methylbenzenesulfonamide Synthesis of AT(l(4Chlorophenyl)lphenylpropyl)tosylamide Synthesis of AT((4Methoxy2methylphenyl)(phenyl)methyl)4 nitrobenzenesulfonamide Application of Pd Catalysts Synthesis of [(4Fluorophenyl)phenylmethyl]carbamic acid tertbv y\ ester Application ofru and Other Catalysts Synthesis of N[(2chlorophenyl)(phenyl)methyl]4methylbenzenesulfonamide Synthesis of Ethyl 2(4(dimethylamino)phenyl)2 ((methoxycarbonyl)amino) acetate The PetasisAkritopoulou Reaction Synthesis of (±)Ar(Diphenylmethyl)aphenylglycine Synthesis of (i?)2((4(benzyloxy)phenyl)(pyrrolidinlyl)methyl)phenol '.4.3 Synthesis of Ethyl 2phenyl2(pyrrolidinlyl)acetate 326 References Carbonyl Group Arylation Introduction Application of Rh Catalysts Additions to Aldehydes Addition to Ketones Application of Pd Catalysts Application of Ru and Other Catalysts Ruthenium Catalysis Nickel Catalysis 357 7'.4.3 Copper Catalysis Platinum Catalysis Iron Catalysis Zinc Catalysis Titanium Catalysis Conclusions Selected Experiments Application of Rh Catalysts Synthesis of (.R)(lNaphthyl)phenylmethanol Synthesis of (S)(2Chlorophenyl)(mesityl)methanol Synthesis of (/?)Benzo[rf] [l,3]dioxol5yl(phenyl)methanol Synthesis of l/7tolyll,2,3,4tetrahydronaphthalenlol Synthesis of (S)5Chloro3(3,5dimethylphenyl)3hydroxyl (4methoxybenzyl)indolin2one Application of Pd Catalysts Synthesis of 3Phenyl3hydroxy2,3dihydrobenzofuran Application of Ru Catalysts Synthesis of (S)(4Chlorophenyl)phenylmethanol Application of Cu Catalysts Synthesis of (S)(4Chlorophenyl)(phenyI)methanol Application of Zn Catalysts 372

7 XIII Contents Synthesis of (#)(Cyclohexyl)phenyImethanoI 372 Synthesis of (i?)2,2dimethyllphenylpropanol 372 Synthesis of l(4'methylphenyl)lphenylethanol 373 References aarylation Processes 376 Introduction 376 Arylation of Enolates and Equivalents 377 Arylation of Ketones and Aldehydes 377 Ketones 377 Aldehydes 397 Arylation of Amides 399 Arylation of Esters 412 Other MetalCatalyzed ctarylations 419 Copper Catalysts 419 Nickel Catalysts 425 Conclusions 427 Selected Experiments 428 Arylation of Enolates and Equivalents 428 Synthesis of 2(4Biphenyl)4methyl3pentanone 428 Synthesis of (x(otolyl)acetophenone 430 Synthesis of lbenzyl4methyll,2,3>4tetrahydro4quinoiinol 430 Synthesis of (i?)l,3dimethyi3phenylindolin2one 430 Synthesis of tertbutyl (6methoxynaphthalen2yl)acetate 430 Synthesis of fertbutyl ocmesitylpropanoate 430 Other MetalCatalyzed aarylations 431 Synthesis of lbenzyl6chloro5fluoro3(lhydroxyethylidene)indolin2one 431 Synthesis of (S)2Phenylloctanol 431 Synthesis of 2Methyl2(4(trifluoromethyl)phenyl)2,3dihydrol//indenlone 431 References Catalytic Cycloaddition Aromatization Processes 436 Introduction 436 Cycloaddition Events 436 [2+2+2] Cycloadditions 436 With Rhodium 437 With Cobalt 443 With Ruthenium 445 With Palladium 448 With Iron 452 With Nickel 452 With Titanium 452 With Iridium 454 With Copper 454 [3+2]Cycloadditions for the Synthesis of Aromatic Compounds 455 The Huigsen's Reaction 455 Tetrazole Synthesis 469 Pyrrole Synthesis 472 The DielsAlder Reaction 474 RadicalBased Cycloaromatization Processes 474

8 Contents XIII The Catalytic Bergman Cyclization The Catalytic MyersSaito Cyclization Conclusions Selected Experiments from the Literature [2+2+2]Cycloaddition RhodiumCatalyzed Synthesis of 2, 4, 5, 7TetraphenylisoindoIine Cobalt Catalyzed Synthesis of 2(2Methoxylnaphthyl)6phenyl7,8dihydro5Hcyclopenta[c]pyridine PalladiumCatalyzed Synthesis of an Aromatic Hexaester IronCatalyzed Synthesis of 3,6Dimethyl2wbutyl pyridine [3+2]Cycloaddition: ClickChemistry CuCatalyzed Synthesis of 17[3(l(l,2,3Triazolyl))]estradiol Organocatalytic Synthesis of l,5diphenyll//l,2,3triazole CuINBSMediated Synthesis of N[5"(Phenylthio)Phosphorylethoxyethyl]2',3'0 isopropylidene5'phosphoryl5il,2,3triazole4amideldribofuranoside RuCatalyzed Synthesis of lbenzyl5phenyll//l,2,3triazole Synthesis of l(2methylbenzyl)5benzoyl tetrazole Catalytic Synthesis of Dimethyl 3CyclopropyllWpyrrole2,4dicarboxylate 486 References 486 Index 491