Regioselective synthesis of aryl hydrazides by palladium-catalyzed coupling of t-butylcarbazate with substituted aryl bromides

Wang, Zhongren; Skerlj, Renato T.; Bridger, Gary

doi:10.1016/s0040-4039(99)00561-4

Cited by 89 publications

(44 citation statements)

References 13 publications

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“…[101] In 2003, Batey reported an intramolecular guanidinylation. [102] Using Pd(PPh 3 ) 4 almost quantitative yields could be achieved, nevertheless the complementary copper iodide-catalyzed process was found to be superior (Scheme 8).…”

Section: Coupling With Sulfoximines Hydrazines and Guanidinesmentioning

confidence: 99%

Palladium‐Catalyzed CN and CO Coupling–A Practical Guide from an Industrial Vantage Point^†

2004

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The palladium-catalyzed coupling of amines with aryl halides or aryl alcohol derivatives, commonly dubbed Buchwald-Hartwig amination, has matured from a synthetic laboratory procedure to a technique that is widely used in natural product synthesis as well as in other fields of academic interest. Furthermore, due to the versatility and reliability of this reaction, researchers in industrial environments have included this methodology in their toolbox as a standard procedure for the synthesis of amine derivatives. Therefore, it is not surprising that first industrial processes up to ton-scale have been performed using this cross-coupling reaction. The authors who are involved in the application of this reaction to industrial processes on this scale give an overview of the recent developments in this field of chemistry, also including fundamental principles, with a special focus on the industrial approach and issues to be considered relevant in scaling-up this transition metal-catalyzed chemistry. This review differs from the already existing excellent academic reviews by focusing on the practical problems arising during implementing the methodology in an industrial environment as well as giving practical hints to this end.

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Section: Coupling With Sulfoximines Hydrazines and Guanidinesmentioning

confidence: 99%

Palladium‐Catalyzed CN and CO Coupling–A Practical Guide from an Industrial Vantage Point^†

2004

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“…It is satisfying to us that moderate to excellent yields ranged from 85% to 98% were obtained for all the combinations. The weak sensitivity to electron effects is very interesting for electron-rich substrates, which are less straight forward by transition-metal-catalyzed reactions [33,34] .…”

Section: Resultsmentioning

confidence: 99%

Bifunctional Salen-Cu(II) complex as efficient catalyst for N-arylation of imidazoles and Suzuki-Miyaura coupling reactions

Wang

Gao

Zhao

et al. 2015

Chem. Res. Chin. Univ.

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Bifunctional Salen-Cu(II) complex catalyzed cross-coupling reactions of aryl halids with imidazoles or phenylboronic acid reagents have been developed as practical methods for C-N and C-C bond formation. The procedure tolerates aryl halides with various functional groups(such as methoxy, acetyl, nitrile, fluoro and nitro groups) and gives the corresponding coupling products in moderate to high yields. The catalyst remained active after five successive catalytic runs without loss in performance.

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“…This weak sensitivity to electronic effects is very interesting with regard to electron-rich substrates, since transitionmetal catalyzed reaction involving these arylating agents are traditionally less straightforward, particularly when metal is palladium. 28,29 N-Arylations are known to be very sensitive to steric hindrance. In our case, the substitution at the ortho position (entries 3 and 5) did not affect the reaction.…”

Section: Hetmentioning

confidence: 99%

PEG3400–Cu2O–Cs2CO3: an efficient and recyclable microwave-enhanced catalytic system for ligand-free Ullmann arylation of indole and benzimidazole

et al. 2010

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Regioselective synthesis of aryl hydrazides by palladium-catalyzed coupling of t-butylcarbazate with substituted aryl bromides

Cited by 89 publications

References 13 publications

Palladium‐Catalyzed CN and CO Coupling–A Practical Guide from an Industrial Vantage Point^†

Palladium‐Catalyzed CN and CO Coupling–A Practical Guide from an Industrial Vantage Point^†

Bifunctional Salen-Cu(II) complex as efficient catalyst for N-arylation of imidazoles and Suzuki-Miyaura coupling reactions

PEG3400–Cu2O–Cs2CO3: an efficient and recyclable microwave-enhanced catalytic system for ligand-free Ullmann arylation of indole and benzimidazole

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Regioselective synthesis of aryl hydrazides by palladium-catalyzed coupling of t-butylcarbazate with substituted aryl bromides

Cited by 89 publications

References 13 publications

Palladium‐Catalyzed CN and CO Coupling–A Practical Guide from an Industrial Vantage Point†

Palladium‐Catalyzed CN and CO Coupling–A Practical Guide from an Industrial Vantage Point†

Bifunctional Salen-Cu(II) complex as efficient catalyst for N-arylation of imidazoles and Suzuki-Miyaura coupling reactions

PEG3400–Cu2O–Cs2CO3: an efficient and recyclable microwave-enhanced catalytic system for ligand-free Ullmann arylation of indole and benzimidazole

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Product

Resources

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Palladium‐Catalyzed CN and CO Coupling–A Practical Guide from an Industrial Vantage Point^†

Palladium‐Catalyzed CN and CO Coupling–A Practical Guide from an Industrial Vantage Point^†