A useful and convenient method for
sp3 C–P(O)
bond formation via direct regioselective hydrophosphinylation of simple
and readily available alkenes using a lanthanum-based N,N-dimethylbenzylamine complex (La(DMBA)3) as a precatalyst
is demonstrated. The reaction proceeds with perfect atom economy for
a wide range of styrenes with secondary phosphine oxides, giving moderate
to excellent yields.
An intermolecular sulfenoamination reaction utilizing a stable sulfur precursor with a broad range of alkene structures is described. More importantly, these reactions proceed in a highly regio- and stereoselective manner to afford interesting heterocyclic motifs ready for biological studies. In addition, a highly regiodivergent approach to access the opposite regioisomers for styrene derivatives was also developed.
We report an attractive and efficient
synthetic approach
to form
Si–N bonds via the heterodehydrocoupling of silanes and amines
catalyzed by a lanthanum-based N,N-dimethylbenzylamine complex [La(DMBA)3]. A wide variety
of primary and secondary amines were well-suited coupling partners
with primary, secondary, and tertiary silanes for this catalytic transformation,
resulting in the formation of numerous silylamines in high efficiency
and moderate-to-excellent yields under mild conditions.
A high-yielding
and atom-efficient protocol for the double hydrophosphorylation
of nitriles using a lanthanum-based N,N-dimethylbenzylamine complex (La(DMBA)3) as a precatalyst
is reported. This method provides a straightforward and convenient
approach for the synthesis of biologically important organophosphorus
compounds known as N-(α-phosphoryl)amidophosphates
in good to excellent yields. Nitriles with a broad range of additional
functionality were tolerated, including those with halides, ethers,
amines, and pyridyl groups.
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