Synthesis of Isonitriles from N-Substituted Formamides Using Triphenylphosphine and Iodine

被引：33

作者：

Wang, Xia ^{[1
]}

Wang, Qing-Gang ^{[1
]}

Luo, Qun-Li ^{[1
]}

机构：

[1] Southwest Univ, Key Lab Appl Chem Chongqing Municipal, Coll Chem & Chem Engn, Chongqing 400715, Peoples R China

来源：

SYNTHESIS-STUTTGART | 2015年 / 47卷 / 01期

基金：

中国国家自然科学基金;

关键词：

isonitriles; formamides; dehydration; triphenylphosphine; iodine; PALLADIUM-CATALYZED SYNTHESIS; ISOCYANIDE INSERTION; DERIVATIVES; REACTIVITY; ACIDS; ALKYL;

D O I：

10.1055/s-0034-1379111

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of N-substituted formamides with the reagent combination of triphenylphosphine and molecular iodine, in the presence of a tertiary amine, quickly produces the corresponding isocyanides in high yields under ambient conditions. The process employs readily available and low-cost reagents, a convenient synthetic procedure, and mild reaction conditions for the synthesis of various alkyl and aryl isocyanides.

引用

页码：49 / 54

页数：6

共 50 条

[1] Hydroamidation of alkenes with N-substituted formamides
Nath, DCD
Fellows, CM
Kobayashi, T
Hayashi, T
AUSTRALIAN JOURNAL OF CHEMISTRY, 2006, 59 (03) : 218 - 224
[2] Trimethylsilyl cyanide affords N-substituted formamides
不详
CHEMICAL & ENGINEERING NEWS, 1996, 74 (38) : 43 - 43
[3] A More Sustainable Isocyanide Synthesis from N-Substituted Formamides Using Phosphorus Oxychloride in the Presence of Triethylamine as Solvent
Salami, Sodeeq Aderotimi
Siwe-Noundou, Xavier
Krause, Rui Werner Macedo
MOLECULES, 2022, 27 (20):
[4] Oxidative amidation of benzaldehydes and benzylamines with N-substituted formamides
Gupta, Shyam Sunder R.
Nakhate, Akhil V.
Rasal, Kalidas B.
Deshmukh, Gunjan P.
Mannepalli, Lakshmi Kantam
NEW JOURNAL OF CHEMISTRY, 2017, 41 (24) : 15268 - 15276
[5] ELECTROLYTIC BENZOYLOXYLATION OF N, N-DISUBSTITUTED FORMAMIDES, N-SUBSTITUTED LACTAMS, AND N-SUBSTITUTED CYCLIC IMIDES
ARITA, S
HIRAI, N
NISHIMUR.Y
TAKESHIT.K
NIPPON KAGAKU KAISHI, 1973, (11) : 2160 - 2165
[6] Visible-light-promoted synthesis of secondary and tertiary thiocarbamates from thiosulfonates and N-substituted formamides
Bi, Wen-Zhu
Zhang, Wen-Jie
Li, Zi-Jie
He, Yuan-Hao
Feng, Su-Xiang
Geng, Yang
Chen, Xiao-Lan
Qu, Ling-Bo
ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (40) : 8701 - 8705
[7] A Novel Method for Preparing Isocyanides from N-Substituted Formamides with Chlorophosphate Compounds
Kobayashi, Genki
Saito, Tateo
Kitano, Yoshikazu
SYNTHESIS-STUTTGART, 2011, (20): : 3225 - 3234
[8] Building formamide and N-substituted formamides from isocyanates on hydrogenated water ices
Tieppo, N.
Redondo, P.
Pauzat, F.
Parisel, O.
Guillemin, J. -C
Ellinger, Y.
ASTRONOMY & ASTROPHYSICS, 2025, 695
[9] Synthesis of N-Substituted Sulfamate Esters from Sulfamic Acid Salts by Activation with Triphenylphosphine Ditriflate
Blackburn, J. Miles
Short, Melanie A.
Castanheiro, Thomas
Ayer, Suraj K.
Muellers, Tobias D.
Roizen, Jennifer L.
ORGANIC LETTERS, 2017, 19 (21) : 6012 - 6015
[10] N-Substituted Formamides as C1-Sources for the Synthesis of Benzimidazole and Benzothiazole Derivatives by Using Zinc Catalysts
Nale, Deepak B.
Bhanage, Bhalchandra M.
SYNLETT, 2015, 26 (20) : 2835 - 2842

← 1 2 3 4 5 →