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Relevant academic research and scientific papers

Cooperative titanocene and phosphine catalysis: Accelerated C-X activation for the generation of reactive organometallics

The study presented herein describes a reductive transmetalation approach toward the generation of Grignard and organozinc reagents mediated by a titanocene catalyst. This method enables the metalation of functionalized substrates without loss of functional group compatibility. Allyl zinc reagents and allyl, vinyl, and alkyl Grignard reagents were generated in situ and used in the addition to carbonyl substrates to provide the corresponding carbinols in yields up to 99%. It was discovered that phosphine ligands effectively accelerate the reductive transmetalation event to enable the metalation of C-X bonds at temperatures as low as -40 °C. Performing the reactions in the presence of chiral diamines and amino alcohols led to the enantioselective allylation of aldehydes.

Highly regioselective control of 1,2-addition of organolithiums to α,β-unsaturated compounds promoted by lithium bromide in 2-methyltetrahydrofuran: A facile and eco-friendly access to allylic alcohols and amines

Very high regioselective 1,2-addition of organolithiums to α,α-unsaturated carbonyl-like compounds (ketones, aldehydes, and imines) in the presence of LiBr was achieved by carrying out reactions in the sustainable solvent 2-methyltetrahydrofuran. Excellent yields (in isolated product) of allylic alcohols and allylic amines were recovered under a simple experimental procedure at 0 °C.

Application of Indium Ate Complexes to Synthetic Chemistry. Selective Conjugate Addition to Enones and Coupling with Allylic Halides

Tetraorganoindium ate complexes, prepared by the addition of organolithium reagents to trialkylindium, reacted with α,β-unsaturated ketones in a 1,4-addition fashion; allylic indates derived from allylic indium sesquihalides coupled with allylic halides regio- and stereo-specifically to give high yields of hed-to-tail 1,5-dienes.

Reactions of Carbonyl Compounds with Grignard Reagents in the Presence of Cerium Chloride

The addition of Grignard reagents to ketones is significantly enhanced by cerium chloride with remarkable supression of side reactions, particularly enolization.Some esters, which are prone to side reactions, also react readily with Grignard reagents in the presence of cerium chloride to give normal reaction products in reasonable to high yields.

CERIUM CHLORIDE-PROMOTED NUCLEOPHILIC ADDITION OF GRIGNARD REAGENTS TO KETONES AN EFFICIENT METHOD FOR THE SYNTHESIS OF TERTIARY ALCOHOLS

In the presence of anhydrous cerium(III) chloride, Grignard reagents react with ketones to afford addition products in high yields, even though the substrates are susceptible to abnormal reactions with Grignard reagents alone.

Carbon-Carbon Bond-Forming Reactions Using Cerium Metal or Organocerium(III) Reagents

Carbon-carbon bond-forming reactions using cerium metal or organocerium(III) reagents have been investigated.Cerium amalgam is an effective reagent for the chemoselective preparation of homoallylic alcohols from allyl halides and carbonyl compounds.These same reagent can also be satisfactorily employed for the Reformatsky-type reaction of α-halo esters with carbonyl compounds.It has been shown that organocerium(III) reagents are conveniently generated by the reaction of organolithiums with cerium(III)iodide or cerium(III)chloride.The reagents are less basic thanorganolithiums or Grignard reagents, and they react cleanly at -78 to -65 deg C with various carbonyl compounds to afford the addition products in high yields, even though the substrates are susceptible to enolization or metal-halogen exchange with simple organolithiums.The same reagents react also with α,β-unsaturated compounds to yield 1,2-addition products in high selectivity.