1263316-76-2Relevant academic research and scientific papers
Hydroaminoalkylation/Buchwald-Hartwig amination sequences for the synthesis of benzo-annulated seven-membered nitrogen heterocycles
Kaper, Tobias,Doye, Sven
, p. 4343 - 4350 (2019)
Reaction sequences consisting of an initial intermolecular titanium-catalyzed hydroaminoalkylation of a suitably ortho-bromophenyl-substituted alkene and a subsequent intramolecular Buchwald-Hartwig amination are used for the synthesis of benzazepine, ben
Linear Hydroaminoalkylation Products from Alkyl-Substituted Alkenes
Warsitz, Michael,Doye, Sven
, p. 15121 - 15125 (2020/10/23)
The regioselective conversion of alkyl-substituted alkenes into linear hydroaminoalkylation products represents a strongly desirable synthetic transformation. In particular, such conversions of N-methylamine derivatives are of great scientific interest, because they would give direct access to important amines with unbranched alkyl chains. Herein, we present a new one-pot procedure that includes an initial alkene hydroaminoalkylation with an α-silylated amine substrate and a subsequent protodesilylation reaction that delivers linear hydroaminoalkylation products with high selectivity from simple alkyl-substituted alkenes. For that purpose, new titanium catalysts have been developed, which are able to activate the α-C?H bond of more challenging α-silylated amine substrates. In addition, a direct relationship between the ligand structure of the new catalysts and the obtained regioselectivity is described.
Fast Titanium-Catalyzed Hydroaminomethylation of Alkenes and the Formal Conversion of Methylamine
Bielefeld, Jens,Doye, Sven
supporting information, p. 6138 - 6143 (2020/03/13)
The scientific interest in catalytic hydroaminoalkylation reactions of alkenes has vastly increased over the past decade, but these reactions have struggled to become a viable option for general laboratory or industrial use because of reaction times of several days. The titanium-based catalytic system introduced in this work not only reduces the reaction time by several orders of magnitude, into the range of minutes, but the catalyst is also demonstrated to be easily available from common starting materials, at a cost of approximately 1 € per millimole of catalyst. We were also able to formally perform C?H activation of methylamine and achieve coupling to a broad variety of alkenes, through silyl protection of the amine and simple deprotection by water.
GROUP 5 METAL COMPLEXES FOR PRODUCING AMINE-FUNTIONALIZED POLYOLEFINS
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Page/Page column 41; 46; 49; 59; 61-63, (2019/12/15)
This application pertains to group 5 metal complexes having the structure of Formula I: and their potential utility in catalyzing amination of polyolefins having alkene groups.amine-
GROUP 5 METAL COMPLEXES FOR CATALYTIC AMINE FUNCTIONALIZATION
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Page/Page column 28; 35; 45; 47-49, (2018/12/14)
This application pertains to group 5 metal complexes having the structure of Formula I; and their potential utility in catalyzing α-alkylation of secondary amine-containing moieties.
Catalytic and Atom-Economic Csp3 ?Csp3 Bond Formation: Alkyl Tantalum Ureates for Hydroaminoalkylation
DiPucchio, Rebecca C.,Ro?ca, Sorin-Claudiu,Schafer, Laurel L.
supporting information, p. 3469 - 3472 (2018/03/21)
Atom-economic and regioselective Csp3 ?Csp3 bond formation has been achieved by rapid C?H alkylation of unprotected secondary arylamines with unactivated alkenes. The combination of Ta(CH2SiMe3)3Clsu
Group 5 metal binaphtholate complexes for catalytic asymmetric hydroaminoalkylation and hydroamination/cyclization
Reznichenko, Alexander L.,Emge, Thomas J.,Audoersch, Stephan,Klauber, Eric G.,Hultzsch, Kai C.,Schmidt, Bernd
scheme or table, p. 921 - 924 (2011/05/04)
3,3′-Silylated binaphtholate tantalum and niobium complexes were shown to be efficient catalysts for the asymmetric hydroaminoalkylation of N-methylaniline derivatives and N-benzylmethylamine with simple alkenes in enantioselectivities of up to 80% ee. No
