863709-49-3Relevant academic research and scientific papers
Ru-catalyzed anti-Markovnikov addition of amides to alkynes: A regio- and stereoselective synthesis of enamides
Goossen, Lukas J.,Rauhaus, Jan E.,Deng, Guojun
, p. 4042 - 4045 (2005)
(Chemical Equation Presented) The base-free anti-Markovnikov addition of secondary amides, anilides, lactams, ureas, bislactams, and carbamates to terminal alkynes is accomplished, for the first time, by a ruthenium-catalyzed reaction. Two complementary p
A practical and effective ruthenium trichloride-based protocol for the regio- and stereoselective catalytic hydroamidation of terminal alkynes
Goossen, Lukas J.,Arndt, Matthias,Blanchot, Mathieu,Rudolphi, Felix,Menges, Fabian,Niedner-Schatteburg, Gereon
supporting information; experimental part, p. 2701 - 2707 (2009/10/06)
A rational catalyst development based on mechanistic and spectroscopic investigations led to the discovery of a new protocol for catalytic hydroamidation reactions that draws on easily available ruthenium trichloride trihydrate (RuCl3·3H2O) as the catalyst precursor instead of the previously employed, expensive bis(2-methylallyl)(1,5- cyclooctadiene) ruthenium(II). This practical and easy-to-use protocol dramatically improves the synthetic applicability of Ru-catalyzed hydroamidations. The catalyst, generated in situ from ruthenium(III) chloride hydrate, tri-n-butylphosphine, 4-(dimethylamino)-pyridine and potassium carbonate, effectively promotes the addition of secondary amides, lactams and carbamates to terminal alkynes under formation of (E)-anti-Markovnikov enamides. The scope of the new protocol is demonstrated by the synthesis of 24 functionalized enamide derivatives, among them valuable intermediates for organic synthesis.
