Preparation and reaction of quinolinyl (or pyridinyl)phosphonium salts with base and pivalaldehyde
α- and γ-Heteroaryltriphenylphosphonium iodides were prepared by reaction of the corresponding heteroaryl iodides with triphenylphosphine. Reaction of β-heteroaryl iodides with triphenylphosphine in the presence of a palladium catalyst gave β-heteroaryltriphenylphosphonium iodides. Elimination of the heteroaryl group was achieved by treating the heteroaryltriphenylphosphonium iodides with a base. Further, the heteroaryl group was trapped with pivalaldehyde to introduce a pivaloyl substituent onto the heteroaromatic ring.
Chemistry of heteroaryltriphenylphosphonium iodides: Preparation from iodoheteroaromatics and elimination of the phosphonium iodide group using basic solvents
α- and γ-Iodoheteroaromatics were found to react with triphenylphosphine to give heteroaromatictriphenylphosphonium iodides in excellent yields, β-lodoheteroaromatics, which are less reactive with triphenylphosphine compared to α- or γ-compounds, were con
Sato, Akihiro,Sugimoto, Osamu,Tanji, Ken-ichi
experimental part
p. 2735 - 2739
(2010/04/25)
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