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Relevant academic research and scientific papers

The Rhodium-Catalyzed Hydroboration of Olefins: A Mechanistic Investigation

Labeling studies carried out on the rhodium-catalyzed olefin hydroboration reaction reveal that the degree of reversibility of the elementary steps in the catalytic cycle is highly substrate dependent.The implications of these observations are discussed.

Direct Carbohydroxylation of Arylalkenes with Allylic Alcohols: Cooperative Catalysis of Copper, Silver, and a Br?nsted Acid

The cooperative catalysis of copper, silver, and Br?nsted acid is presented as a new strategy for olefin functionalization. The catalytic direct carbohydroxylation of arylalkenes with allylic alcohols provided a straightforward and efficient approach for preparing 4,5-unsaturated alcohols. Synthetically useful functional groups, such as Cl, Br, carbonyl, and chloromethyl, remained intact during the functionalization reaction.

New amine-stabilized deuterated borane-tetrahydrofuran complex (BD3-THF): convenient reagent for deuterium incorporations

Convenient methods for the preparation of BD3-THF complex were developed. Certain amines stabilize the BD3-THF for long-term storage. Regioselectivity studies were carried out with the new amine-stabilized BD3-THF with rep

Functionalized organolithium compounds of DTBB-catalyzed sulfur-lithium exchange

The successive reaction of β- or γ-hydroxy or amino phenyl thioethers (1,4) with butyllithium and an excess of lithium powder in the presence of a catalytic amount of DTBB in THF at - 78°C leads to the formation of the corresponding β- or γ-functionalized organolithium compounds 2 or 5, respectively, which by treatment with different electrophiles [D2O, t- BuCHO, PhCHO, Me2CO, (CH2)4CO, (CH2)5CO] at temperatures ranging between - 78°C and room temperature yields, after hydrolysis with water, the expected functionalized alcohols or amines 3 or 6, respectively, in a completely regioselective manner.

β-Functionalised organolithium compounds through a sulfur-lithium exchange

The successive reaction of different β-hydroxy or β-amino tbioethers 1a-d with n-butyl-lithium and an excess of lithium powder and a catalytic amount of DTB in THF at -78°C leads to the formation of the corresponding β-functionalised organolithium compounds 2a-d, which by reaction with several electrophiles [D2O, Bu(t)CHO, PhCHO, Me2CO, (CH2)5CO] at temperatures ranging between -78 and 20°C yields, after hydrolysis with water, the expected functionalised alcohols or amines 3aa-de in a regioselective manner.

β-Substituted Organolithium Compounds from Chlorohydrins: Application to the Direct Synthesis of Bifunctionalized Organic Cpmpounds

The reaction of different chlorohydrins with n-butyl-lithium at -78 deg C followed by metallation wiht lithium naphthalenide at the same temperature leads to very reactive organolithium compounds bearing an alkoxide function at the β-position with respect to metal.The reaction of these intermediates with several electriphiles leads to mono- as well as bi-functionalized organic compounds.Thus, treatment of these dianions with deuterium oxide, oxygen, carbon dioxide, benzyl bromide, dimethyl disulphide, and carbonyl compounds, gave 2-deuterioalcohols, 1,2-diols, β-hydroxy-acids, 2-benzyl alcohols, 2-hydroxy-thioethers, and 1,3-diols respectively.The preparation of β-substituted organolithium derivatives can be alternatively carried out starting from α-chloroketones by the same procedure.When the lithium atom is linked to a secondary carbon atom the dianions are very unstable and decompose, even at -100 deg C, by β-elimination yielding the corresponding olefins.

β-Substituted Organolithium Compounds; Direct Preparation and Reactivity

Very reactive organolithium compounds bearing an alkoxide function at the β-position with respect to the metal are obtained by direct metallation with lithium naphthalenide at low temperature of the corresponding lithium chlorohydrin salt; the reaction of these dianions with different electrophilic agents leads to the corresponding mono- and bi-functionalized compounds.