Topic
Alkylation
About: Alkylation is a research topic. Over the lifetime, 29915 publications have been published within this topic receiving 464944 citations. The topic is also known as: alkylation reaction.
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TL;DR: Experimental and computational studies support that N-phenoxyacetamides most likely undergo an initial ortho-C-H alkylation with diazo compounds via a Rh( III)-catalyzed C-H activation, and the resulting Rh(III) intermediate subsequently undergoes an intramolecular oxidative addition into the O-N bond to form a Rh (V) nitrenoid species.
Abstract: A Rh(III)-catalyzed unsymmetrical C–H alkylation and amidation of N-phenoxyacetamides with diazo compounds has been developed under mild and redox-neutral conditions, producing dinitrogen as the only byproduct. The reaction represents the first example of one-step, unsymmetrical difunctionalization of two ortho-C–H bonds. Experimental and computational studies support that N-phenoxyacetamides most likely undergo an initial ortho-C–H alkylation with diazo compounds via a Rh(III)-catalyzed C–H activation, and the resulting Rh(III) intermediate subsequently undergoes an intramolecular oxidative addition into the O–N bond to form a Rh(V) nitrenoid species that is protonated and further directed toward electrophilic addition to the second ortho position of the phenyl ring. This work might provide a new direction for unsymmetrical C–H difunctionalization reactions in an efficient manner.
108 citations
TL;DR: A chemoselective, direct nucleophilic C2-functionalization pathway could be developed for the synthesis of indoline compounds, as proposed in Equation (1; Nu = nucleophile), although such a synthetic approach has not yet been addressed.
Abstract: Indoles bearing a tethered internal olefin smoothly undergo a highly efficient diastereoselective intramolecular imino-ene reaction in the presence of AlCl3 to give cycloalkano-fused indolines, e.g. (II), (IV) or (VI), in high yields and stereoselectivities.
108 citations
TL;DR: Palladium complexes of the chiral diphosphanes 1 and 2 which possess a rigid backbone and a large bite angle catalyze the alkylation of allyl compounds with both high enantioselectivities and reaction rates, particularly with less sterically demanding substrates.
Abstract: Palladium complexes of the chiral diphosphanes 1 and 2 which possess a rigid backbone and a large bite angle catalyze the alkylation of allyl compounds with both high enantioselectivities and reaction rates, particularly with less sterically demanding substrates. 1: R=Me, X=S; 2: R=H, X=C(CH3 )2 .
108 citations
TL;DR: In this paper, the effect of substitution on the olefin, the acetylene, and the tether connecting the two was probed in terms of the effect on the ODE.
Abstract: A Pd(0)-catalyzed alkylation of an allyl substrate with a nucleophile containing a double or triple bond to permit subsequent thermal Alder ene reactions constitutes a novel annulation protocol. In the case of a triple bond, a Pd(2+) complex catalyzes an equivalent of an Alder ene reaction. This new cyclization is probed in terms of the effect of substitution on the olefin, the acetylene, and the tether connecting the two. The reaction produces both 1,4-dienes (Alder ene-type products) and 1,3-dienes. Mechanisms to account for the diversity of products are presented. The Pd(2+)-catalyzed reaction shows an ability to interact with remote nonreactive parts of substrates to affect conformation and thereby selectivity. Several advantages accrue to the Pd(2+)-catalyzed reaction
108 citations
TL;DR: A straightforward process for the N-alkylation of amines has been developed applying readily available carboxylic acids and silanes as the hydride source and allows obtaining a broad range of alkylated secondary and tertiary amines, including fluoroalkyl-substituted anilines.
Abstract: A straightforward process for the N-alkylation of amines has been developed applying readily available carboxylic acids and silanes as the hydride source. Complementary to known reductive aminations, effective C–N bond construction proceeds under mild conditions and allows obtaining a broad range of alkylated secondary and tertiary amines, including fluoroalkyl-substituted anilines as well as the bioactive compound Cinacalcet HCl.
108 citations