- Anodic Oxidation of Aminotetrazoles: A Mild and Safe Route to Isocyanides
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A new electrochemical method for the preparation of isocyanides from easily accessible aminotetrazole derivatives has been developed, which tolerates an unprecedented range of functional groups. The use of chemical, rather than electrochemical, oxidation to afford isocyanides was also demonstrated, which provides access to these compounds for those without electrosynthesis equipment. The practicality of scale-up using flow electrochemistry has been demonstrated, in addition to the possibility of using electrochemically generated isocyanides in further reactions.
- Leech, Matthew C.,Petti, Alessia,Tanbouza, Nour,Mastrodonato, Andrea,Goodall, Iain C. A.,Ollevier, Thierry,Dobbs, Adrian P.,Lam, Kevin
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p. 9371 - 9375
(2021/12/09)
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- One-pot synthesis of isocyanides from alcohols
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A one-pot reaction of alcohols with trimethylsilyl cyanide and methanesulfonic acid with subsequent neutralization by triethylamine and dehydration by tosyl chloride and pyridine gave the corresponding isocyanides in moderate-to-high yields. This method was used to synthesize tertiary and benzylic isocyanides from the corresponding alcohols. Georg Thieme Verlag Stuttgart · New York.
- Okada, Iku,Kitano, Yoshikazu
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experimental part
p. 3997 - 4002
(2012/01/06)
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- Isocyanide-based multicomponent reaction 'without' isocyanides
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We present here a one-pot, four-component sequence that affords Ugi-type adducts starting from simple benzyl or allyl bromides. The isocyanides are prepared in situ under alkylation of silver cyanide salts and the resulting mixture is directly used in a U
- El Kaim, Laurent,Grimaud, Laurence,Schiltz, Aurélie
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experimental part
p. 1401 - 1404
(2009/10/19)
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- One-pot synthesis of oxazoles using isocyanide surrogates
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We wish to present herein a simple one-pot synthesis of 2,5-disubstituted oxazoles, starting from benzyl halides and acyl chlorides. The in situ formation of isocyanides, followed by the addition of an acyl chloride in the presence of a base leads to the
- Kaim, Laurent El,Grimaud, Laurence,Schiltz, Aurélie
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experimental part
p. 5235 - 5237
(2009/12/06)
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- A convenient method for the preparation of benzyl isocyanides
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Treatment of benzyl halides with silver salts (AgClO4, AgBF 4, or AgOTf) and trimethylsilyl cyanide (TMSCN) in CH 2Cl2 followed by cleavage of the carbon-silicon bond with aqueous NaHCO3 or TBAF directly afforded the corresponding isocyanides. Georg Thieme Verlag Stuttgart.
- Kitano, Yoshikazu,Manoda, Tetsuya,Miura, Teppei,Chiba, Kazuhiro,Tada, Masahiro
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p. 405 - 410
(2007/10/03)
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