Synthesis of amides through the Cannizzaro-type reaction catalyzed by lanthanide chlorides

Zhang, Lijun; Su, Shunpeng; Wu, Huayue; Wang, Shaowu

doi:10.1016/j.tet.2009.09.101

Cited by 35 publications

(18 citation statements)

References 31 publications

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“…Amidation of urethane protected a-amino acids containing 9-uorenylmethyloxycarbonyl (Fmoc), benzyloxycarbonyl (Cbz), and tert-butyloxycarbonyl (Boc) groups (entries [17][18][19] was found to proceed without protecting group removal and no signicant racemization was observed based on chiral HPLC analysis of the optically active products.…”

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confidence: 99%

An efficient mechanochemical synthesis of amides and dipeptides using 2,4,6-trichloro-1,3,5-triazine and PPh₃

et al. 2015

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confidence: 99%

An efficient mechanochemical synthesis of amides and dipeptides using 2,4,6-trichloro-1,3,5-triazine and PPh₃

et al. 2015

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“…N , N ‐Diethylbenzylamine (5c): Yield 72 %, 1 H NMR (500 MHz): δ = 7.35–7.28 (m, 5 H), 3.48 (br., 2 H), 3.18 (br., 2 H), 1.17 (br., 3 H), 1.04 (br., 3 H) ppm. 13 C NMR (125 MHz): δ = 171.3, 137.3, 129.1, 128.4, 126.3, 43.3, 39.2, 14.2, 12.9 ppm.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of Amides from Alcohols and Amines Through a Domino Oxidative Amidation and Telescoped Transamidation Process

Drageset

Bjørsvik

2018

Eur J Org Chem

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The amide bond formation is of paramount importance in organic synthesis, both within academic research and industrial development and manufacturing of pharmaceutical chemicals and other biologically active compounds. Despite this fact, as well as the ever‐increasing treatment costs of side streams and other environmental concerns regarding handling and transportation of hazardous reagents, contemporary synthesis has elicited few new reactions and methods for the preparation of amides. Herein, we reveal a high yielding and expedite two‐step telescoped synthetic process that comprises a domino oxidative amidation and transamidation for the creation of amides. The process utilizes alcohols and amines as reaction pairs with TEMPO and Fe ions as catalytic system and 1,3‐dichloro‐5,5‐dimethyl hydantoin as a terminal oxidant. The oxidative amidation and transamidation process is conducted under benign reaction conditions and short reaction time (≈ 30 min.) in a two‐step telescoped fashion by means of a multi‐jet oscillating disk (MJOD) continuous‐flow reactor platform. The disclosed process integrates alcohol oxidation and amide formation to afford target amide in yields up to 90 %. The method operates with both primary and secondary amines together, but was hampered when bulky amines and/or alcohols were used as reagent/substrate.

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“…156-157 °C (lit. 20 156-157 °C); 1 H NMR (400 MHz, CDCl 3 ) δ 7.79 (s, 1H), 7.84 (d, J = 7.7 Hz, 2H), 7.41-7.53 (m, 5H), 7.17 (d, J = 8.1 Hz, 2H), 2.33 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ 165.9, 135.4, 135.0, 134.2, 131.6, 129.5, 128.6, 127.1, 120.5, 20.9; HRMS (ESI) calcd for C 14 H 13 NO: 211.0997; found: 211.0105.…”

Section: Methodsmentioning

confidence: 99%

Base-promoted synthesis of N-arylbenzamides by N-benzoylation of dimethylphenylthioureas

Liu

Zeng

et al. 2017

Journal of Chemical Research

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An efficient synthesis of 10 N-arylbenzamides was achieved by N-benzoylation of N,N-dimethyl-( N′-phenyl)thioureas with 4-substituted benzoyl chlorides in dimethylacetamide in the presence of K2CO3. The features of this method include good yields, short reaction times and broad substrate scope. This work showed that arylthiourea derivatives can be alternative and useful starting materials for the preparation of N-arylbenzamides.

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Synthesis of amides through the Cannizzaro-type reaction catalyzed by lanthanide chlorides

Cited by 35 publications

References 31 publications

An efficient mechanochemical synthesis of amides and dipeptides using 2,4,6-trichloro-1,3,5-triazine and PPh₃

An efficient mechanochemical synthesis of amides and dipeptides using 2,4,6-trichloro-1,3,5-triazine and PPh₃

Synthesis of Amides from Alcohols and Amines Through a Domino Oxidative Amidation and Telescoped Transamidation Process

Base-promoted synthesis of N-arylbenzamides by N-benzoylation of dimethylphenylthioureas

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Synthesis of amides through the Cannizzaro-type reaction catalyzed by lanthanide chlorides

Cited by 35 publications

References 31 publications

An efficient mechanochemical synthesis of amides and dipeptides using 2,4,6-trichloro-1,3,5-triazine and PPh3

An efficient mechanochemical synthesis of amides and dipeptides using 2,4,6-trichloro-1,3,5-triazine and PPh3

Synthesis of Amides from Alcohols and Amines Through a Domino Oxidative Amidation and Telescoped Transamidation Process

Base-promoted synthesis of N-arylbenzamides by N-benzoylation of dimethylphenylthioureas

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An efficient mechanochemical synthesis of amides and dipeptides using 2,4,6-trichloro-1,3,5-triazine and PPh₃

An efficient mechanochemical synthesis of amides and dipeptides using 2,4,6-trichloro-1,3,5-triazine and PPh₃