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Multi‐Component Synthesis of Rare 1,3‐Dihydro‐1,3‐azaborinine Derivatives: Application of a Bora‐Nazarov Type Reaction
Author(s) -
Li Jun,
Daniliuc Constantin G.,
MückLichtenfeld Christian,
Kehr Gerald,
Erker Gerhard
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201909530
Subject(s) - chemistry , isocyanide , hydroboration , ring (chemistry) , insertion reaction , medicinal chemistry , component (thermodynamics) , molar ratio , closure (psychology) , stereochemistry , organic chemistry , catalysis , physics , economics , market economy , thermodynamics
The twofold hydroboration products of (Fmes)BH 2 ⋅SMe 2 with a series of alkynes (2‐butyne, arylethynes) react with two molar equiv of 2,6‐dimethylphenyl isocyanide (CN‐Xyl) at 80 °C to give rare examples of 1,3‐azaborinine derivatives. A mechanistic study revealed a reaction course involving insertion of one isonitrile followed by a bora‐Nazarov type ring‐closure reaction and subsequent isonitrile insertion to give the respective 1,3‐dihydro‐1,3‐azaborinines 5 .
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