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Relevant academic research and scientific papers

Ureate Titanium Catalysts for Hydroaminoalkylation: Using Ligand Design to Increase Reactivity and Utility

Hydroaminoalkylation describes the atom-economical catalytic synthesis of amines by forming new Csp3-Csp3 bonds using readily available amine and alkene feedstocks. Herein, we describe an earth-abundant and cost-efficient titanium catalyst generated in si

Linear Hydroaminoalkylation Products from Alkyl-Substituted Alkenes

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

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.

Planar-Chiral [2.2]Paracyclophane-Based Pyridonates as Ligands for Tantalum-Catalyzed Hydroaminoalkylation

By using planar chiral [2.2]paracyclophane-containing N,O-chelating ligands for tantalum-catalyzed hydroaminoalkylation, one of the most versatile catalytic systems for this reaction to date was obtained. Convenient Csp3?Csp3 bond fo

GROUP 5 METAL COMPLEXES FOR PRODUCING AMINE-FUNTIONALIZED POLYOLEFINS

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

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

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

Ligand Effects and Kinetic Investigations of Sterically Accessible 2-Pyridonate Tantalum Complexes for Hydroaminoalkylation

The synthesis of a series of structurally varied pyridonate-supported tantalum amido complexes and their catalytic reactivity in the intermolecular α-alkylation of unprotected secondary amines are described. Both terminal and internal alkenes can undergo

In Situ Generation of a Regio- and Diastereoselective Hydroaminoalkylation Catalyst Using Commercially Available Starting Materials

The design of an easy to use catalyst system for the regio- and diastereoselective intermolecular hydroaminoalkylation of alkenes with secondary amines is reported. The method utilizes commercially available ligands and tantalum starting materials, and does not require the isolation of air and water sensitive organometallic complexes. The in situ prepared catalyst is active toward a variety of secondary amine substrates, including those with ethyl substituents which yield α- and β-alkylated amines as a single diastereomer. This catalytic transformation can be used to prepare amines containing functionality that promotes ring closure to achieve the diastereoselective synthesis of di- and trialkylated N-heterocycles.

Intermolecular hydroaminoalkylation of alkenes and dienes using a titanium mono(formamidinate) catalyst

An easily accessible formamidinate ligand-bearing titanium complex initially synthesized by Eisen et al. is used as catalyst for intermolecular hydroaminoalkylation reactions of unactivated, sterically demanding 1,1- and 1,2-disubstituted alkenes and styr