28541-43-7Relevant academic research and scientific papers
Titanium-catalyzed iminohydrazination of alkynes
Banerjee, Sanjukta,Shi, Yanhui,Cao, Changsheng,Odom, Aaron L.
, p. 5066 - 5077 (2005)
Titanium pyrrolyl complexes Ti(NMe2)2(dap) 2 (1), where dap is 2-(N,N-dimethylaminomethyl)pyrrolyl, and Ti(NMe2)3(bap) (3), where bap is 2,5-bis(N,N- dimethylaminomethyl)pyrrolyl, were found to be eff
Ruthenium-Catalyzed Enantioselective Hydrogenation of Hydrazones
Chen, Song,Dropinski, James F.,Li, Hongming,Schuster, Christopher H.,Shevlin, Michael
supporting information, p. 7562 - 7566 (2020/10/09)
Prochiral hydrazones undergo efficient and highly selective hydrogenation in the presence of a chiral diphosphine ruthenium catalyst, yielding enantioenriched hydrazine products (up to 99% ee). The mild reaction conditions and broad functional group tolerance of this method allow access to versatile chiral hydrazine building blocks containing aryl bromide, heteroaryl, alkyl, cycloalkyl, and ester substituents. This method was also demonstrated on >150 g scale, providing a valuable hydrazine intermediate en route to an active pharmaceutical ingredient.
Bis(amidate)bis(amido) titanium complex: A regioselective intermolecular alkyne hydroamination catalyst
Yim, Jacky C.-H.,Bexrud, Jason A.,Ayinla, Rashidat O.,Leitch, David C.,Schafer, Laurel L.
, p. 2015 - 2028 (2014/04/03)
An efficient and selective bis(amidate)bis(amido) titanium precatalyst for the anti-Markovnikov hydroamination of alkynes is reported. Hydroamination of terminal and internal alkynes with primary alkylamines, arylamines, and hydrazines is promoted by 5-10 mol % of Ti catalyst. Various functional groups are tolerated including esters, protected alcohols, and imines. The in situ generated complex shows comparable catalytic activity, demonstrating its synthetic versatility for benchtop application. Applications of this catalyst for the synthesis of amino alcohols and a one-pot procedure for indole synthesis are described. A mechanistic proposal that invokes turnover-limiting protonolysis is presented to rationalize the observed regioselectivities.
Palladium catalyzed cyclizations of oxime esters with 1,2-disubstituted alkenes: Synthesis of dihydropyrroles
Race, Nicholas J.,Bower, John F.
supporting information, p. 4616 - 4619 (2013/09/24)
Pd-catalyzed cyclizations of oxime esters with 1,2-dialkylated alkenes provide an entry to chiral dihydropyrroles. Substrate and catalyst controlled strategies for selective product formation (vs alternative pyrroles) are outlined.
Uncatalyzed Strecker-type reaction of N,N-dialkylhydrazones in pure water
Marques-Lopez, Eugenia,Herrera, Raquel P.,Fernandez, Rosario,Lassaletta, Jose M.
supporting information; experimental part, p. 3457 - 3460 (2009/04/08)
Aldehyde and ketone N,N-dialkylhydrazones behave as a stable class of imine surrogates exhibiting a unique reactivity in the Strecker reaction with in situ generated HCN, that proceeds in pure water in the absence of co-solvents, catalysts or promoters. E
Rh(I) and Ir(I) catalysed intermolecular hydroamination with substituted hydrazines
Dabb, Serin L.,Messerle, Barbara A.
supporting information; experimental part, p. 6368 - 6371 (2009/02/08)
The catalysed intermolecular hydroamination of a series of terminal alkynes with substituted hydrazines was achieved using Rh(i) and Ir(i) complexes.
Intermolecular alkyne hydroaminations involving 1,1-disubstituted hydrazines
Cao, Changsheng,Shi, Yanhui,Odom, Aaron L.
, p. 2853 - 2856 (2007/10/03)
(figure presented) Two readily prepared catalysts have been developed for the hydroamination of alkynes by 1,1-disubstituted hydrazines. The catalyses are facile with terminal alkynes and some internal alkynes. If the hydrazine bears an aryl group, Fische
