TY - JOUR
T1 - Alkynyl Fischer Carbenes as a Platform for the Production of Difluorodiazaborinine Complexes via β-Amino-azadienes
AU - Benítez-Puebla, Luis J.
AU - López, Julio
AU - Flores-Álamo, Marcos
AU - Cruz, David Cruz
AU - Peña-Cabrera, Eduardo
AU - Delgado, Francisco
AU - Tamariz, Joaquín
AU - Vázquez, Miguel A.
N1 - Publisher Copyright:
© 2019 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
PY - 2019/10/17
Y1 - 2019/10/17
N2 - 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).
AB - 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).
KW - Alkynyl Fischer carbenes
KW - Diflourodiazaborinine
KW - β-Amino carbenes
KW - β-Amino-1-azadiene
UR - http://www.scopus.com/inward/record.url?scp=85073512148&partnerID=8YFLogxK
U2 - 10.1002/ejoc.201901047
DO - 10.1002/ejoc.201901047
M3 - Artículo
AN - SCOPUS:85073512148
SN - 1434-193X
VL - 2019
SP - 6571
EP - 6578
JO - European Journal of Organic Chemistry
JF - European Journal of Organic Chemistry
IS - 38
ER -