Transition-metal-free oxidative amidation of benzyl alcohols with amines catalyzed by NaI: a new method for the synthesis of benzamides

Karimi, Meghdad; Saberi, Dariush; Azizi, Kobra; Arefi, Marzban; Heydari, Akbar

doi:10.1016/j.tetlet.2014.07.085

Cited by 30 publications

(8 citation statements)

References 67 publications

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“…They rely on the combination of either NaI or DIB (diacetoxyiodobenzene) with TBHP in order to afford efficient oxidant systems. 152,153 Hence, NaI (10 mol %) was able to catalyze the synthesis of benzamides from aromatic alcohols and primary and secondary amine hydrochloride salts in the presence of TBHP (8.0 equiv), CaCO 3 (2.2 equiv) in acetonitrile at 80 °C under argon (18 examples, 53−93% yields) (Scheme 55a). 152 The use of few enantiomerically pure amines afforded the desired products in a racemization-free process.…”

Section: Redox and Oxidative Amidations With Organo-and Metal-catalystsmentioning

confidence: 99%

Nonclassical Routes for Amide Bond Formation

2016

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The present review offers an overview of nonclassical (e.g., with no pre- or in situ activation of a carboxylic acid partner) approaches for the construction of amide bonds. The review aims to comprehensively discuss relevant work, which was mainly done in the field in the last 20 years. Organization of the data follows a subdivision according to substrate classes: catalytic direct formation of amides from carboxylic and amines ( section 2 ); the use of carboxylic acid surrogates ( section 3 ); and the use of amine surrogates ( section 4 ). The ligation strategies (NCL, Staudinger, KAHA, KATs, etc.) that could involve both carboxylic acid and amine surrogates are treated separately in section 5 .

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Section: Redox and Oxidative Amidations With Organo-and Metal-catalystsmentioning

confidence: 99%

Nonclassical Routes for Amide Bond Formation

2016

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“…Discrete hypervalent iodine reagents, such as diacetoxy iodobenzene [145] and those generated in-situ (from KI, [146] NaI, [147] and TBAI [148] ), have recently been described as another class of oxidative amidation catalysts. These catalysts could couple either methyl arenes [146] or benzylic alcohols [147][148][149] and aldehydes [149] with alkyl…”

Section: Hypervalent Iodinementioning

confidence: 99%

Recent developments in catalytic amide bond formation

Todorovic

Perrin

2020

Peptide Science

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Amide bond forming reactions are critical for both polypeptide synthesis and medicinal chemistry. Most current approaches for amidation employ stoichiometric activating agents, but such methods are neither atom economical nor synthetically elegant. Catalytic approaches for amidation are potentially green and more ideal substitutes for current standard methods and thus are the subject of this review. Such methods face significant thermodynamic and kinetic barriers and have, as a result, historically

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“…The existing metal‐free catalytic systems for the direct amidation of alcohols usually involve iodine species. Thus, secondary and tertiary benzamides can be obtained by reaction of benzyl alcohols and amine hydrochlorides in the presence of catalytic NaI (10 mol %) and TBHP as the oxidant at 60–100 °C and 4 h . Furthermore, application of a I 2 or TBAI catalyst with aqueous TBHP as an oxidant allows the combination of various alcohols with N , N ‐disubstituted formamides (Scheme ) .…”

Section: Overview Of Recent Advances In Chemospecific One‐pot Transfmentioning

confidence: 99%

Recent Advances in Cascade Reactions Initiated by Alcohol Oxidation

2016

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In this review, we attempt to answer the question: how can we construct complex functionalized molecules with significant added value from cheap and readily available alcohols in the simplest and most efficient manner? Accordingly, recent developments (mainly from the last five years) in the field of one‐pot multiple transformations of alcohols are overviewed in terms of process simplification and optimization; sustainability; and atom, bond, step, and redox economy. Particular attention is paid to chemo‐ and stereoselective transformations with specific formation of particular bonds and configurations, leaving other parts of substrates unchanged.

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Transition-metal-free oxidative amidation of benzyl alcohols with amines catalyzed by NaI: a new method for the synthesis of benzamides

Cited by 30 publications

References 67 publications

Nonclassical Routes for Amide Bond Formation

Nonclassical Routes for Amide Bond Formation

Recent developments in catalytic amide bond formation

Recent Advances in Cascade Reactions Initiated by Alcohol Oxidation

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