New aryl/heteroaryl CN bond cross-coupling reactions via arylboronic acid/cupric acetate arylation

Lam, Patrick Y.S.; Clark, C. G.; Saubern, Simon; Adams, Jessica; Winters, Michael P.; Chan, Dominic M. T.; Combs, Andrew P.

doi:10.1016/s0040-4039(98)00504-8

Cited by 998 publications

(488 citation statements)

References 13 publications

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“…In all attempts, biphenyl was formed instead of the desired N-arylation product (3 a). However, copper catalysts turned out to be effective, even at room temperature, and CuCl was found to give the best yield when K 3 PO 4 was used as the base ( [17][18].…”

Section: Dedicated To Professor Xiyan Lu On the Occasion Of His 80th mentioning

confidence: 99%

Aryl Halide Tolerated Electrophilic Amination of Arylboronic Acids with N‐Chloroamides Catalyzed by CuCl at Room Temperature

et al. 2008

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Dedicated to Professor Xiyan Lu on the occasion of his 80th birthdayTransition-metal-catalyzed aryl C sp2 ÀN bond formation has been intensively studied over the past decade because of the importance of the amines and their derivatives in chemistry related fields.[1-9] The Pd-or Cu-catalyzed formation of anilines from electrophilic aryl halides and nucleophilic primary or secondary amines, pioneered by Buchwald and co-workers and Louie and Hartwig, as well as others, [10][11][12][13][14] is a hallmark reaction in this field. In 1998, Chan et al., Evans et al., and Lam et al. independently developed Cu-mediated oxidative amination of nucleophilic arylboronic acids with amines or other nucleophiles, [16][17][18][19][20] and the methods were later improved to include catalytic versions. [15,17,21,22] However, electrophilic amination of organometallic reagents by R 1 R 2 N + synthons, [23][24][25][26][27][28][29][30][31] though conceptually feasible, has received much less attention. [32][33][34][35][36][37] The putative catalytic cycle of this transformation is illustrated in Scheme 1: (1) reaction of R 1 R 2 N À X (as an electrophile) with the metal catalyst (M 1 ) would introduce the amine group to the metal center to form R 1 R 2 N-M 1 -X; [34][35][36][37][38][39][40][41][42][43][44][45][46][47][48] (2) transmetalation of RM 2 (M 2 = B(OH) 2 ) with R 1 R 2 N-M 1 -X to furnish R 1 R 2 N-M 1 R; and (3) final reductive elimination to form the CÀN bond.The groups of Liebeskind and Johnson have studied this type of CÀN bond formation employing NÀO derivatives. [32][33][34][35][36][37] N-Chloroamides, though attractive because of the ease of preparation [49][50][51] and the high activities of the N À Cl bond, [23,50,51] have seldom been utilized in catalytic electrophilic amination reactions. To the best of our knowledge, Göttlich et al. has primarily studied the Cu-mediated reaction of N-chloroamines with alkenes. [38,39,52] Herein, we communicate our results regarding ligandless copper-catalyzed electrophilic amination of arylboronic acids by N-chloroamides under mild conditions.Our initial experiments of N-chloro-N-phenylacetamide [49] (1 a) and phenylboronic acid (2 a) were carried out by using palladium catalysts. In all attempts, biphenyl was formed instead of the desired N-arylation product (3 a).

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Section: Dedicated To Professor Xiyan Lu On the Occasion Of His 80th mentioning

confidence: 99%

Aryl Halide Tolerated Electrophilic Amination of Arylboronic Acids with N‐Chloroamides Catalyzed by CuCl at Room Temperature

et al. 2008

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“…7 Commercially obtained L-tyrosine 3 was brominated at 3-position with bromine in acetic acid and hydrobromic acid in acetic acid at room temperature to afford 3-bromo-L-tyrosine hydrobromide 4 9 in 95 % yield from 3. Compound 4 was N-protected with a Boc group and methylated with dimethyl sulphate (2.5 eq.)…”

Section: Resultsmentioning

confidence: 99%

Formal synthesis of piperazinomycin, a novel antifungal antibiotic

Ghosh¹,

Kumar²,

Mehta³

et al. 2009

Arkivoc

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“…17 Unfortunately these methods have several limitations and in an attempt to overcome their limitations (long reaction times, using harsh conditions and solvents that are not eco-friendly), [18][19][20][21] Lam-Chan developed a protocol based on the use of copper (II) acetate and boronic acids. [22][23] It takes advantage of the convenient, well-known properties of arylboronic acids: stability, structural diversity and lower toxicity. 24 This article reports studies on the N-arylation of 2,4-dichloro-7H-pyrrolo [2,3-d]pyrimidine (Table 1), using a simple modified Lam-Chan conditions.…”

Section: Figure 1 Structures Of N-aryl-pyrrolomentioning

confidence: 99%

A convenient and simple synthesis of N-aryl-pyrrolopyrimidines using boronic acids and promoted by copper (II) acetate

Espinosa‐Bustos¹,

Villegas²,

Salas³

2017

Arkivoc

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New aryl/heteroaryl CN bond cross-coupling reactions via arylboronic acid/cupric acetate arylation

Cited by 998 publications

References 13 publications

Aryl Halide Tolerated Electrophilic Amination of Arylboronic Acids with N‐Chloroamides Catalyzed by CuCl at Room Temperature

Aryl Halide Tolerated Electrophilic Amination of Arylboronic Acids with N‐Chloroamides Catalyzed by CuCl at Room Temperature

Formal synthesis of piperazinomycin, a novel antifungal antibiotic

A convenient and simple synthesis of N-aryl-pyrrolopyrimidines using boronic acids and promoted by copper (II) acetate

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