Premium
Construction of Halofunctionalized Indenes via a Cascade Prins‐Nazarov Cyclization Promoted by Dual Roles of BX 3
Author(s) -
Sultana Sabera,
Lee Yong Rok
Publication year - 2020
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201901266
Subject(s) - chemistry , halogenation , boron , cascade , nucleophile , regioselectivity , combinatorial chemistry , medicinal chemistry , organic chemistry , catalysis , chromatography
Halofunctionalization of various unactivated arylalkynes to the corresponding 1H ‐indenes in the presence of a particular class of carboxaldehydes and boron trihalides (BX 3 , X=F, Cl, Br, I) is described. A diverse array of halofunctionalized indenes substituted with a heterocycle has been synthesized regioselectively with BX 3 as a promotor for the carbocyclization and a source of X − for halogenation. This reaction proceeds via a formal halogenative [4+1] cycloaddition between arylalkynes and carboxaldehydes promoted by boron trihalides to generate halofunctionalized indenes. The usefulness of the halofunctionalized indenes was demonstrated by their conversion to other derivatives via coupling, nucleophilic substitution, and oxidation.