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CpTiCl 2 ‐Catalyzed Cross‐Coupling between Internal Alkynes and Ketones: A Novel Concept in the Synthesis of Halogenated, Conjugated Dienes
Author(s) -
RoldanMolina Esther,
Nievas Maria M.,
Navarro Jorge A. R.,
Oltra J. Enrique
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202001023
Subject(s) - sonogashira coupling , alkyne , conjugated system , conjugate , chemistry , catalysis , reactivity (psychology) , diene , combinatorial chemistry , organic chemistry , coupling reaction , palladium , medicine , mathematical analysis , natural rubber , alternative medicine , mathematics , pathology , polymer
Abstract A novel concept for the synthesis of halogenated, conjugated dienes is disclosed: the CpTiCl 2 ‐catalyzed coupling of keto‐alkynes, in the presence of Me 3 SiBr/Et 3 N ⋅ HBr. This reaction provided five‐, six‐, and seven‐membered carbocycles, nitrogenated heterocycles, as well as six‐membered oxygenated heterocycles leading to a brominated conjugate diene. These products showed high reactivity in the Diels–Alder, Suzuki, and Sonogashira reactions, giving complex chemical structures in only three steps from the corresponding acyclic keto‐alkyne. Hopefully, this strategy will pave the way towards the synthesis of bioactive natural products and new materials.

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