Efficient silylformylation of alkynes catalyzed by rhodium complexes with P,N donor ligands

Alonso, M.; Casares, Juan A.; Espinet, Pablo; Vallés, Elena; Soulantica, Katerina

doi:10.1016/s0040-4039(01)01086-3

Cited by 13 publications

(1 citation statement)

References 23 publications

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“…Alonso and co-workers [28] compared the behaviour of several neutral and cationic rhodium(I) complexes with P, N donor ligands in the catalysis of the silylformylation of 1-hexyne with Et 3 SiH (Scheme 17). All the tested compounds catalysed the reaction under atmospheric pressure of CO affording exclusively the expected (Z)-β-silylalkenal.…”

Section: Rhodium Catalystsmentioning

confidence: 99%

Synthesis and Reactivity of Silylformylation Products Derived from Alkynes

2008

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The silylformylation reaction of unsaturated compounds consists of the rhodium-catalysed addition of a R 3 Si and a CHO moiety to a carbon-carbon multiple bond. The silylformylation process is applicable to both terminal and internal alkynes and is tolerant towards several functional groups. Many factors can influence the chemoselectivity of the reaction that generally affords β-silylalkenals with high yields and regioselectivity. The β-silylalkenals are polyfunctionalised substrates that can be submitted to several chemical transformations and in particular can undergo fluoride-promoted (TBAF) aryl migration from an aryldimethylsilyl group to the adjacent carbon atom thus generating 2-(arylmethyl)-aldehydes, important industrial precursors of perfumes. This silylformylation-aryl migration two-steps sequence can be applied to functionalised alkyne precursors and chemo-, regio-and stereoselectivity of the products can be modulated according to the nature and the position of the functional

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Section: Rhodium Catalystsmentioning

confidence: 99%