Low-valent titanium() mediated intramolecular and regioselective alkyne/alkoxyallene reductive coupling reactions

Low-valent titanium( ii ) complexes turned out to be suitable reagents in the promotion of alkyne/alkoxyallene coupling reactions in an intramolecular fashion. The conditions developed herein led to a broad range of highly functionalized cyclic adducts with excellent regioselectivities toward the ce...

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Published inChemical communications (Cambridge, England) Vol. 6; no. 13; pp. 1786 - 1789
Main Authors Bodinier, Florent, Lannou, Marie-Isabelle, Sorin, Geoffroy
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 08.02.2024
Royal Society of Chemistry
Subjects
Adducts
Alkynes
Chemical reactions
Chemical Sciences
Chemistry
Chemistry, Multidisciplinary
Coupling
Physical Sciences
Reagents
Regioselectivity
Science & Technology
Titanium
ALCOHOLS
ETHERS
REAGENTS SELECTIVITY ISSUES
TITANIUM(IV) ALKOXIDES
REACTIVITY
STEREOSELECTIVE-SYNTHESIS
ALLENES
COMBINATION
DERIVATIVES
CYCLIZATION
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Summary:Low-valent titanium( ii ) complexes turned out to be suitable reagents in the promotion of alkyne/alkoxyallene coupling reactions in an intramolecular fashion. The conditions developed herein led to a broad range of highly functionalized cyclic adducts with excellent regioselectivities toward the central carbon of the alkoxyallene moiety. Good yields (up to 76%) were obtained over 19 examples. One-pot late functionalization by electrophile trapping was also possible and led to excellent diastereoselectivities (up to 95/5 d.r.). Low-valent titanium( ii ) complexes turned out to be suitable reagents in the promotion of alkyne/alkoxyallene coupling reactions in an intramolecular fashion.
Bibliography:https://doi.org/10.1039/d3cc06084e
Electronic supplementary information (ESI) available. See DOI
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SourceType-Scholarly Journals-1
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ISSN:1359-7345
1364-548X
1364-548X
DOI:10.1039/d3cc06084e