91909-17-0Relevant articles and documents
Palladium-Catalyzed One-Pot Conversion of Aldehydes and Ketones into 4-Substituted Homopropargyl Alcohols and 5-En-3-yn-1-ols ?
Umana, Christian A.,Cabezas, Jorge A.
, p. 9505 - 9514 (2017)
Sequential treatment of 2,3-dichloropropene with magnesium and n-BuLi generated the equivalent of 1,3-dilithiopropyne, which adds regiospecifically to aldehydes and ketones to produce homopropargyl alcohols. The lithium acetylide intermediate formed in this protocol can be further reacted with aromatic and vinyl halides, under palladium catalysis, to produce 4-substituted homopropargyl alcohols and 5-en-3-yn-1-ols, respectively, in one-pot with good overall yields.
Efficient propargylation of aldehydes and ketones catalyzed by titanocene(III)
Justicia, Jose,Sancho-Sanz, Iris,Alvarez-Manzaneda, Enrique,Oltra, J. Enrique,Cuerva, Juan M.
experimental part, p. 2295 - 2300 (2009/12/27)
We describe a novel method for the propargylation of a wide range of aldehydes and ketones catalyzed by titanocene(III) complexes under mild reaction conditions and compatible with many functional groups. Homopropargylic alcohols are obtained as the sole products even when ketones are used as starting materials, which is unusual in Barbier-type propargylations.
A new method for the preparation of 1,3-dilithiopropyne: An efficient synthesis of homopropargyl alcohols
Cabezas, Jorge A,Pereira, Albán R,Amey, Adam
, p. 6819 - 6822 (2007/10/03)
Controlled dilithiation of propargyl bromide with two equivalents of n-butyllithium, in the presence of TMEDA, produces the operational equivalent of the dianion 1,3-dilithiopropyne. The latter reacts efficiently with aldehydes and ketones to produce homo
Propargylation of carbonyl compounds: An efficient method for the synthesis of homopropargyl alcohols
Cabezas, Jorge A.,Alvarez, Leonardo X.
, p. 3935 - 3938 (2007/10/03)
Controlled dilithiation of allene, with two equivalents of n- butyllithium, produces the propargyl dianion 5. The latter couples efficiently with carbonyl compounds to produce homopropargyl alcohol in high yields.