fatty amines from triglycerides.Figure 9.47 Synthesis of fatty amides and nitriles from triglycerides.Figure 9.48 Synthesis of long‐chain diamines from long‐chain diols by direct...10 Chapter 10Scheme 10.1 Historic strategies for the synthesis of aromatic amines.Scheme 10.2 Transition‐metal‐based methodologies for the preparation of arom...Scheme 10.3 (a) Ullmann's (1903) and (b) Goldberg's (1906) initial reports o...Scheme 10.4 Anticipated mechanism of the copper‐catalyzed C–N coupling react...Scheme 10.5 Examples of different conditions for the copper‐catalyzed C—N bo...Scheme 10.6 Examples of different modifications of the Ullmann C—N bond form...Scheme 10.7 Preparation of synthetic naphthalenoid H3 antagonist 9 on a 14.5...Scheme 10.8 Synthesis of pyrazole 12 by large‐scale Ullmann coupling.Scheme 10.9 Preparation of annulated aniline derivative 14 as an intermediat...Scheme 10.10 Industrial‐scale synthesis of N‐cyclopropyl pyrazole derivative...Scheme 10.11 Migita's early report on a palladium‐catalyzed C–N coupling rea...Scheme 10.12 Buchwald's and Hartwig's initial reports of a palladium‐catalyz...Scheme 10.13 Mechanistic cycle of the palladium‐catalyzed C–N coupling react...Scheme 10.14 Evolution of the ligands for the Buchwald–Hartwig amination rea...Scheme 10.15 Preparation of N‐p‐tolyl‐substituted benzophenone hydrazine der...Scheme 10.16 Preparation of intermediate 23 for the synthesis of a 5‐HT rece...Scheme 10.17 C–N coupling of pyridazinium chloride 24 and amino pyrazole 25....Scheme 10.18 Regioselective and enantiospecific C–N coupling of isoquinoline...Scheme 10.19 Preparation of the precursor 32 for AMG 925 by Amgen.Scheme 10.20 Aromatic C—N bond formation approaches.Scheme 10.21 Palladium‐catalyzed aryl C–H amination.Scheme 10.22 Rhodium‐catalyzed direct C–H amination with aryl azides.Scheme 10.23 Synthetic versatility of diarylamine products from C–H aminatio...Scheme 10.24 Rhodium‐catalyzed C–H amination and synthetic utilities.Scheme 10.25 C–H amination enabled by a dirhodium catalyst.Scheme 10.26 Diarylamine synthesis via iridium‐nitrenoid catalyzed C–H amina...Scheme 10.27 Nickel‐catalyzed aryl C–H amination with alkyl amines.Scheme 10.28 Long‐standing challenge of using ammonia as an aminating agent ...Scheme 10.29 Nickel‐mediated C–H amination with ammonia.Scheme 10.30 Cobalt‐catalyzed aryl C–H amination and directing group hydroly...Scheme 10.31 Amination of benzylamine picolinamide.Scheme 10.32 Copper‐catalyzed C—N bond formation using dibenzothiophene sulf...Scheme 10.33 Copper‐catalyzed primary aniline synthesis.Scheme 10.34 Iron‐catalyzed C–H functionalization using ammonia surrogate 34Scheme 10.35 Organocatalyic C–H oxidative amination.Scheme 10.36 Typical modes of action of photocatalysis.Scheme 10.37 Synthesis of anilines enabled by a photoredox acridinium cataly...Scheme 10.38 Photoredox‐catalyzed C–H amination: substrate scope.Scheme 10.39 Reaction scope of ruthenium‐catalyzed C–H amination.Scheme 10.40 Synthesis of aniline derivatives via a sequence of C–H pyridina...Scheme 10.41 Photocatalytic amination of benzene with 37.Scheme 10.42 Aniline synthesis via electrochemical C–H amination.Scheme 10.43 Electrochemical C–H amination by cobalt catalysis. (a) Lei's sy...Scheme 10.44 Copper‐mediated decarboxylative amination of 38.Scheme 10.45 Palladium‐catalyzed decarboxylative couplings.Scheme 10.46 C–H amination under Pd/Cu dual catalysis.Scheme 10.47 Nickel‐catalyzed amination of aryl/heteroaryl chlorides.Scheme 10.48 Ni(NHC)‐catalyzed amination of aryl/heteroaryl chlorides.Scheme 10.49 Nickel‐catalyzed amination of aryl chlorides using silane reduc...Scheme 10.50 First example of room temperature nickel‐catalyzed amination of...Scheme 10.51 Nickel‐catalyzed amination of aryl/heteroaryl chlorides with pr...Scheme 10.52 Comparison of (a) Stradiotto's and (b) Hartwig's nickel‐catalyz...Scheme 10.53 Gram‐scale, nickel‐catalyzed amination of 2‐naphthyl bromide.Scheme 10.54 Nickel‐catalyzed amination of electrophilic coupling partners o...Scheme 10.55 C–F amination of N-PMB-protected paroxetine (top) and a liquid ...Scheme 10.56 Nickel‐catalyzed C–N couplings developed by Buchwald.Scheme 10.57 Nickel‐catalyzed amination of phenols via C–O activation.Scheme 10.58 Nickel‐catalyzed amination of aryl fluorosulfonates.Scheme 10.59 Cadmium‐catalyzed amination of iodobenzene.Scheme 10.60 Iron‐catalyzed amination of aryl halides.Scheme 10.61 Cobalt‐catalyzed amination of N‐aromatic‐2‐chlorides.Scheme 10.62 Rhodium‐catalyzed amination of bromobenzene derivatives.Scheme 10.63 Copper‐mediated amination of arylsilanes.Scheme 10.64 B(C6F5)3–H2O‐catalyzed reductive amination using silane reducta...Scheme 10.65 Palladium‐catalyzed reduction and reductive amination of nitroa...Scheme 10.66 Metal‐free reductive amination using hydrosilanes.Scheme 10.67 Gold‐catalyzed intermolecular hydroamination of allenes with ar...Scheme 10.68 Enantioselective rhodium‐catalyzed hydroamination of monosubsti...Scheme 10.69 Copper‐catalyzed hydroamination of phenylallene.Scheme 10.70 Enantioselective hydroamination of alkynes by Au(I)/...Scheme 10.71 Copper‐catalyzed asymmetric hydroamination.Scheme 10.72 Enantioselective copper‐catalyzed hydroamination of styrene wit...Scheme 10.73 Copper‐catalyzed anti‐Markovnikov hydroamination of vinylarenes...Scheme 10.74 Synthesis of indoline via Cu‐catalyzed hydroamination/Pd‐cataly...Scheme 10.75 Buchwald's flow synthesis of biarylamines and imatinib 46.Scheme 10.76 Meadows' continuous synthesis of arylamine 49 with bulky NHC pr...Scheme 10.77 Continuous‐flow SNAr of heterocycles with nitrogen nucleophiles...Scheme 10.78 (a) Stepwise and (b) one‐pot synthesis with two C—N bond format...Scheme 10.79 Continuous synthesis of pyrazole 55 with a SNAr reaction.Scheme 10.80 Continuous synthesis of cumidine via nitration and hydrogenatio...Scheme 10.81 Catalytic Chan–Lam reaction in continuous flow developed by Bax...Scheme 10.82 C–N coupling of secondary amine with supported SPhos.Scheme 10.83 Selected examples of supported NHC‐Pd catalysts.
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