Synthetic applications and methodology development of Chan–Lam coupling: a review

Munir, Iqra; Zahoor, Ameer Fawad; Rasool, Nasır; Naqvi, Syed Ali Raza; Zia, Khalid Mahmood; Ahmad, Raheel

doi:10.1007/s11030-018-9870-z

Cited by 79 publications

(53 citation statements)

References 79 publications

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“…It was observed that when the Cu(OAc) 2 equivalents were less than one, the reaction did not proceed to completion. This result is in line with most Chan-Lam coupling procedures in the literature, [37] where a stoichiometric amount of copper is required. Overall, the optimised conditions were determined to be 1 eq.…”

Section: Resultssupporting

confidence: 89%

Mechanochemical Synthesis of N‐Aryl Amides from O‐Protected Hydroxamic Acids

et al. 2020

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Two robust and efficient mechanochemical protocols for the synthesis of an array of N‐arylamides have been developed. This was achieved by a C−N cross‐coupling between O‐pivaloyl hydroxamic acids and aryl iodides or aryl boronic acids, in the presence of a stoichiometric amount of a copper mediator. The effectiveness of this method is highlighted by the high‐yielding (up to 94 %), scalable (up to 8 mmol), and rapid (20 minutes) synthesis of N‐aryl amides (15 examples), using a variety of deactivated and sterically encumbered substrates, whilst employing mild conditions and in the absence of solvents. In addition, it was determined that whilst the O‐pivaloyl hydroxamic acid precursors can be synthesised mechanochemically, iron contamination originating from the steel jars was found to occur which can hinder the efficacy of this process. Furthermore, 3D printing was used to produce custom milling jars that could successfully accommodate a scaled‐up version of the two protocols.

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Section: Resultssupporting

confidence: 89%

Mechanochemical Synthesis of N‐Aryl Amides from O‐Protected Hydroxamic Acids

et al. 2020

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“…Air is routinely used for the reaction as an oxidant. The CEL coupling later was elaborated to allow C−N, C−O, C−S, C−Se, C−P bond formation via copper(II)‐catalyzed pathways of arylboronic acids with a wide range of nucleophiles, including sensitive substrates, which is critically important in numerous commercial chemical processes . There are several reports for three‐component, tandem CEL‐type reactions and heterocycles synthesis .…”

Section: Introductionmentioning

confidence: 99%

Chan‐Evans‐Lam C−N Coupling Promoted by a Dinuclear Positively Charged Cu(II) Complex. Catalytic Performance and Some Evidence for the Mechanism of CEL Reaction Obviating Cu(III)/Cu(I) Catalytic Cycle

et al. 2020

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In the present study, we report the synthesis of a series of copper(II) complexes with a wide range of ligands and their testing in the copper catalyzed Chan‐Evans‐Lam (CEL) coupling of aniline and phenylboronic acid. The efficiency of the coupling was directly connected with the ease of the reduction of Cu(II) to Cu(I) of the complexes. The most efficient catalyst was derived from 4‐t‐butyl‐2,5‐bis[(quinolinylimino)methyl]phenolate and two Cu(II) ions. Depending on the counter‐anion nature and the concentration of the reaction mixture, the reaction can be directed to predominant C−N‐bond formation. Forty‐three derivatives of diphenylamine were prepared under the optimized conditions. The proposed mechanism of the catalysis was based on the reduction potential of a series of complexes, molecular weight measurements of the catalytic complex in MeOH and the kinetic studies of aniline and phenylboronic acid coupling. In addition, an 1H NMR experiment in a sealed NMR tube, without external oxygen supply available, proved that no complete Cu(II) to Cu(I) conversion was observed under the condition, ruling out the usually accepted mechanism of the C−N coupling, which included the oxygenation of the intermediately formed Cu(I) complexes after the key step of C−N conversion had already been completed. Instead, a mechanism was proposed, involving an oxygen molecule coordinated to two copper ions in the key C−N bond formation without any detectable conversion of the Cu(II) complexes to Cu(I).

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“…Organoboron compounds have been recognized as extremely useful and readily accessible synthetic intermediates in organic synthesis for many decades -from Nobelprize-winning works of Brown on organoboranes, 1,2 to palladium-catalyzed reaction of boronic acids developed by Suzuki (also awarded with the Nobel prize) 3,4 and more recent discoveries like Chan-Lam 5 and radical photoredox couplings of trifluoroborates. 6 Much attention has been given to the increasing utility of organoboron compounds as building blocks in the construction of complex molecules (for recent general reviews, see [7][8][9][10] ).…”

Section: Introductionmentioning

confidence: 99%

Cycloadditions of Alkenylboronic Derivatives

et al. 2020

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The literature on cycloaddition reactions of boron-containing alkenes is surveyed with 132 references. The data are categorized according to the reaction type ([2+1], [2+2], [3+2], [4+2], and [4+3] cycloadditions). The cyclopropanation and the Diels–Alder reactions of alkenylboronic derivatives have been studied more or less comprehensively, and for some substrates, they can be considered as convenient methods for the rapid regio- and stereoselective construction of even complex cyclic systems. Other types of the cycloadditions, as well as mechanistic aspects of the processes, have been addressed less thoroughly in the previous works.1 Introduction2 [2+1] Cycloaddition2.1 Cyclopropanation2.1.1 With Methylene Synthetic Equivalents2.1.2 With Substituted Carbenoids2.2 Epoxidation2.3 Aziridination3 [2+2] Cycloaddition4 [3+2] Cycloaddition4.1 With Nitrile Oxides4.2 With Diazoalkanes4.3 With Nitrones4.4 With Azomethine Ylides5 [4+2] Cycloaddition6 [4+3] Cycloaddition7 Conclusions and Outlook

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Synthetic applications and methodology development of Chan–Lam coupling: a review

Cited by 79 publications

References 79 publications

Mechanochemical Synthesis of N‐Aryl Amides from O‐Protected Hydroxamic Acids

Mechanochemical Synthesis of N‐Aryl Amides from O‐Protected Hydroxamic Acids

Chan‐Evans‐Lam C−N Coupling Promoted by a Dinuclear Positively Charged Cu(II) Complex. Catalytic Performance and Some Evidence for the Mechanism of CEL Reaction Obviating Cu(III)/Cu(I) Catalytic Cycle

Cycloadditions of Alkenylboronic Derivatives

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