The Buchwald–Hartwig Amination After 25 Years

Dorel, Ruth; Grugel, Christian P.; Haydl, Alexander M.

doi:10.1002/ange.201904795

Cited by 68 publications

(15 citation statements)

References 195 publications

(186 reference statements)

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“…The typical approach for the N -arylation of amines, including nitrogen-containing heteroaromatic compounds, involves the use of transition-metal-catalyzed reactions ( Scheme 1 ). In these cases, Ullman condensation [ 23 , 24 , 25 ], Buchwald–Hartwig amination [ 26 , 27 , 28 ], and Chan–Lam coupling [ 29 , 30 , 31 ] are all frequently used. A common feature of these procedures is the reaction of amines with organohalides or boronic acids in the presence of a transition metal catalyst and a base.…”

Section: Introductionmentioning

confidence: 99%

Recent Progress Concerning the N-Arylation of Indoles

et al. 2021

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This review summarizes the current state-of-the-art procedures in terms of the preparation of N-arylindoles. After a short introduction, the transition-metal-free procedures available for the N-arylation of indoles are briefly discussed. Then, the nickel-catalyzed and palladium-catalyzed N-arylation of indoles are both discussed. In the next section, copper-catalyzed procedures for the N-arylation of indoles are described. The final section focuses on recent findings in the field of biologically active N-arylindoles.

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Section: Introductionmentioning

confidence: 99%

Recent Progress Concerning the N-Arylation of Indoles

et al. 2021

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“…Transition-metal-catalyzed cross-couplings have become the most established modern methods for arylamine synthesis, but require selective prefunctionalization of the aromatic substrate, incurring synthetic cost. 3 Many recent advances have been made in directed transition-metal-catalyzed C–H amination of arenes. 4 Several methods for ortho -selective C–H amination of aniline derivatives have been reported, generating variously N -substituted o -phenylenediamine derivatives, using Pd, 5 Cu, 6 Ru, 7 Ir, 8 and Co 9 catalysis.…”

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confidence: 99%

Regioselective Radical Arene Amination for the Concise Synthesis of ortho-Phenylenediamines

2021

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The formation of arene C–N bonds directly from C–H bonds is of great importance and there has been rapid recent development of methods for achieving this through radical mechanisms, often involving reactive N -centered radicals. A major challenge associated with these advances is that of regiocontrol, with mixtures of regioisomeric products obtained in most protocols, limiting broader utility. We have designed a system that utilizes attractive noncovalent interactions between an anionic substrate and an incoming radical cation in order to guide the latter to the arene ortho position. The anionic substrate takes the form of a sulfamate-protected aniline and telescoped cleavage of the sulfamate group after amination leads directly to ortho -phenylenediamines, key building blocks for a range of medicinally relevant diazoles. Our method can deliver both free amines and monoalkyl amines allowing access to unsymmetrical, selectively monoalkylated benzimidazoles and benzotriazoles. As well as providing concise access to valuable ortho -phenylenediamines, this work demonstrates the potential for utilizing noncovalent interactions to control positional selectivity in radical reactions.

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“…Synthesis and ground state structure N-p-Fluorophenyl-BBTTs were prepared according to our previously published procedure 28 by twofold Buchwald-Hartwig amination [32][33][34] (Scheme 2). (1,1′-bis(dicyclohexylphosphano)ferrocene) was employed as a ligand, and compound 7 DPPF (1,1′bis(diphenylphosphano)ferrocene) was used as a ligand).…”

Section: Resultsmentioning

confidence: 99%