A trustworthy mechanochemical route to isocyanides

被引：8

作者：

Basoccu, Francesco ^{[1
]}

Cuccu, Federico ^{[1
]}

Casti, Federico ^{[1
]}

Mocci, Rita ^{[1
]}

Fattuoni, Claudia ^{[1
]}

Porcheddu, Andrea ^{[1
]}

机构：

[1] Univ Cagliari, Dipartimento Sci Chim & Geol, Cittadella Univ, I-09042 Cagliari, Italy

来源：

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 18卷

关键词：

green chemistry; isocyanide; isonitriles; mechanochemistry; ONE-POT SYNTHESIS; DEHYDRATION; AMIDES; ISONITRILES; NITRILES; CHLORIDE; REAGENT;

D O I：

10.3762/bjoc.18.73

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Isocyanides are hardly produced, dramatically sensitive to purification processes, and complex to handle as synthetic tools. Notwithstanding, they represent one of the most refined and valuable compounds for accessing sophisticated and elegant synthetic routes. A unique interest has always been addressed to their production, though their synthetic pathways usually involve employing strong conditions and toxic reagents. The current paper intends to provide a conceptually innovative synthetic protocol for mechanochemical isocyanide preparation, simultaneously lowering the related reagents' toxicity and improving their purification in a straightforward procedure.

引用

页码：732 / 737

页数：6

共 47 条

[11]

Hofmann A.W., 1970, GRUNDLAGEN ORGANISCH

[12]

Hoy D. J., 1965, US ARMY EDGEWOOD ARS

[13] Synthesis of isocyanides through dehydration of formamides using XtalFluor-E [J].

Keita, Massaba ;

Vandamme, Mathilde ;

Mahe, Olivier ;

Paquin, Jean-Francois .

TETRAHEDRON LETTERS, 2015, 56 (02) :461-464

[14] MICROWAVE SPECTRA AND MOLECULAR STRUCTURES OF METHYL CYANIDE AND METHYL ISOCYANIDE [J].

KESSLER, M ;

RING, H ;

TRAMBARULO, R ;

GORDY, W .

PHYSICAL REVIEW, 1950, 79 (01) :54-56

[15] Mechanochemical Preparation of 3,5-Disubstituted Hydantoins from Dipeptides and Unsymmetrical Ureas of Amino Acid Derivatives [J].

Konnert, Laure ;

Gonnet, Lori ;

Halasz, Ivan ;

Suppo, Jean-Simon ;

de Figueiredo, Renata Marcia ;

Campagne, Jean-Marc ;

Lamaty, Frederic ;

Martinez, Jean ;

Colacino, Evelina .

JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (20) :9802-9809

[16] Multicomponent mechanochemical synthesis [J].

Leonardi, Marco ;

Villacampa, Mercedes ;

Carlos Menendez, J. .

CHEMICAL SCIENCE, 2018, 9 (08) :2042-2064

[17]

Lieke W., 1859, ANN CHEM PHARM, V112, P316

[18] Odorless Isocyanide Chemistry: One-Pot Synthesis of Heterocycles via the Passerini and Postmodification Tandem Reaction Based on the in Situ Capture of Isocyanides [J].

Liu, Na ;

Chao, Fei ;

Liu, Ming-Guo ;

Huang, Nian-Yu ;

Zou, Kun ;

Wang, Long .

JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (04) :2366-2371

[19]

Marquarding D., 1971, Isonitrile Chemistry, P133

[20] 1,1′-Carbonyldiimidazole and Mechanochemistry: A Shining Green Combination [J].

Metro, Thomas-Xavier ;

Martinez, Jean ;

Lamaty, Frederic .

ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2017, 5 (11) :9599-9602

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