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Alkynyl Fischer Carbenes as a Platform for the Production of Difluorodiazaborinine Complexes via β‐Amino‐azadienes
Author(s) -
BenítezPuebla Luis J.,
López Julio,
FloresÁlamo Marcos,
Cruz David Cruz,
PeñaCabrera Eduardo,
Delgado Francisco,
Tamariz Joaquín,
Vázquez Miguel A.
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201901047
Subject(s) - chemistry , stereoselectivity , catalysis , combinatorial chemistry , copper , reaction conditions , organic chemistry
The results of a study of the reactivities of alkynyl Fischer carbenes in the syntheses of diazaborinine derivatives 7a‐i are reported. The strategy employed included the use of β‐amino‐α,β‐unsaturated carbenes ( 3a–j ) with different amines in order to determine the scope of a previously unknown catalytic reaction in the presence of copper salts and anilines. The reaction was highly stereoselective, yielding ( Z )‐isomers of the β‐amino‐1‐azadiene framework as the main products ( 4a–o ). As an extension of this research, the compounds 4a–o proved to be suitable precursors for the syntheses of diazaborinine scaffolds in good yields ( 7a‐i ).