Palladium- and Nickel-Catalyzed Aminations of Aryl Imidazolylsulfonates and Sulfamates

Ackermann, Lutz; Sandmann, René; Song, Weifeng

doi:10.1021/ol200267b

Cited by 116 publications

(60 citation statements)

References 54 publications

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“…Ethyl‐4‐anilinobenzoate : cololess solid; mp 109.1–109.4 °C (lit . 111 °C); IR (neat) 582, 693, 750, 768, 806, 845, 960, 1019, 1109, 1173, 1249, 1271, 1334, 1364, 1407, 1475, 1495, 1528, 1587, 1676, 1687, 2965, 3338, 3365; 1 H NMR (400 MHz, CDCl 3 ), δ=1.38 (t, 3H), 4.33 (q, 2H), 7.00 (d, 2H), 7.06 (t, 1H), 7.17 (d, 2H), 7.33 (t, 2H), 7.92 (d, 2H); 13 C NMR (100 MHz, CDCl 3 ) δ=14.4, 60.4, 114.5, 120.2, 121.3, 123.0, 129.4, 131.3, 140.9, 148.0, 166.5.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of Arylamines via Non‐Aerobic Dehydrogenation Using a Palladium/Carbon‐Ethylene System

2018

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The reaction of cyclohexanones with amines proceeded under an ethylene atmosphere in the presence of a catalytic amount of palladium/carbon to afford a variety of arylamines in good to high yields. The present reaction was carried out under completely non-aerobic conditions, and which is in contrast with the previously reported aerobic system. has wide applicability affording a variety of aromatic amines, and coproduct of the reaction is only gaseous ethane. Thus, this method is environmentally friendly. This protocol was applied intramolecularly to provide a novel method for the construction of quinoline and isoquinoline compounds.

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Section: Methodsmentioning

confidence: 99%

Synthesis of Arylamines via Non‐Aerobic Dehydrogenation Using a Palladium/Carbon‐Ethylene System

2018

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“…Ackermann and coworkers found that the catalyst system composed of Ni(cod) 2 /dppf was suitable for the amination of aryl sulfamates with anilines and problematic primary alkyl amines 54. Reactions proceeded efficiently at 105 °C in the presence of NaO t Bu with 5 mol% catalyst.…”

Section: Amination Of Phenol‐derived Electrophilesmentioning

confidence: 99%

Ni‐Catalyzed Amination Reactions: An Overview

Marín

Rama

Nicasio

2016

The Chemical Record

127

106

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Nitrogen-containing organic compounds are valuable in many fields of science and industry. The most reliable method for the construction of C(sp(2) )-N bonds is undoubtedly palladium-catalyzed amination. In spite of the great achievements made in this area, the use of expensive Pd-based catalysts constitutes an important limitation for large-scale applications. Since nickel is the least expensive and most abundant among the group 10 metals, the interest in Ni-based catalysts for processes typically catalyzed by palladium has grown considerably over the last few years. Herein, we revise the development of Ni-catalyzed amination reactions, emphasizing the most relevant and recent advances in the field.

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“…Phenols are typically protected by various groups to enhance their leaving ability in cross-coupling reactions [ 1 , 2 , 3 ]. Thus, phenols have usually been converted to their corresponding aryl C-O electrophiles, such as fluoroalkylsulfonates [ 4 , 5 ], sulfamates [ 6 , 7 , 8 ], sulfonates [ 9 , 10 , 11 , 12 ], carbonates [ 13 , 14 , 15 ], carbamates [ 16 , 17 ], ethers [ 18 ], phosphoramides, phosphonium salts, phosphates, and pivalates [ 19 , 20 , 21 , 22 ]. Besides the preferable availability of phenol derivatives, this method also proves to be cost-effective, as well as an efficient reaction route to form C-C bonds, C-N bonds, and C-H bonds ( Scheme 1 ) [ 23 , 24 , 25 , 26 , 27 , 28 ].…”

Section: Introductionmentioning

confidence: 99%

Convenient Method of Synthesizing Aryloxyalkyl Esters from Phenolic Esters Using Halogenated Alcohols

Jiang

Zhou

et al. 2018

Molecules

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A facile one-pot synthetic method of building aryloxyalkyl esters was developed using various types of phenolic esters with halogenated alcohols. The ready availability of both starting materials, coupled with the required simple experimental technique, enables the current synthetic method of producing aryloxyalkyl esters in a fast and efficient way. It is noteworthy that acyl transfer was demonstrated in this reaction.

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Palladium- and Nickel-Catalyzed Aminations of Aryl Imidazolylsulfonates and Sulfamates

Abstract: A nickel complex derived from dppf, along with NaOt-Bu as the base, allowed for challenging aminations of aryl sulfamates. An improved functional group tolerance is observed in novel palladium-catalyzed aminations of imidazolylsulfonates with rac-BINAP as the ligand.

Cited by 116 publications

References 54 publications

Synthesis of Arylamines via Non‐Aerobic Dehydrogenation Using a Palladium/Carbon‐Ethylene System

Synthesis of Arylamines via Non‐Aerobic Dehydrogenation Using a Palladium/Carbon‐Ethylene System

Ni‐Catalyzed Amination Reactions: An Overview

Convenient Method of Synthesizing Aryloxyalkyl Esters from Phenolic Esters Using Halogenated Alcohols

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