84735-50-2

Upstream product

• 451-40-1 phenyl benzyl ketone 
• 109-72-8 n-butyllithium 
• 1009-14-9 phenyl butyl ketone 
• 1589-82-8 phenylmagnesium bromide 
• 591-50-4 iodobenzene 
• 25870-62-6 1-phenyl-2-hexanone 
• 5281-18-5 benzaldehyde, hydrazone 
• 102632-99-5 1-phenyl-4-penten-1-ol 
• 100-52-7 benzaldehyde 
• 108-90-7 chlorobenzene 
• 860252-32-0 1,2-diphenyl-hex-5-en-3-yn-2-ol 

Relevant academic research and scientific papers

Synergistic Relay Reactions To Achieve Redox-Neutral α-Alkylations of Olefinic Alcohols with Ruthenium(II) Catalysis

Herein, we report a ruthenium-catalyzed redox-neutral α-alkylation of unsaturated alcohols based on a synergistic relay process involving olefin isomerization (chain walking) and umpolung hydrazone addition, which takes advantage of the interaction between the two rather inefficient individual reaction steps to enable an efficient overall process. This transformation shows the compatibility of hydrazone-type “carbanions” and active protons in a one-pot reaction, and at the same time achieves the first Grignard-type nucleophilic addition using olefinic alcohols as latent carbonyl groups, providing a higher yield of the corresponding secondary alcohol than the classical hydrazone addition to aldehydes does. A broad scope of unsaturated alcohols and hydrazones, including some complex structures, can be successfully employed in this reaction, which shows the versatility of this approach and its suitability as an alternative, efficient means for the generation of secondary and tertiary alcohols.

Benzotriazole-mediated [1,2]-Wittig rearrangement. The preparation of homoalcohols from ethers

α-(Benzotriazol-1-yl)alkyl benzyl ethers (6a-e) undergo [1,2]-Wittig rearrangement upon treatment with 2 equiv of organolithium reagents.

Barbier-type reactions of aryl halides with ketones mediated by Samarium diiodide

Barbier-type reaction of aryl halides with ketones took place on treatment with samarium diiodide in benzene containing 10% hexamethylphosphoric triamide (HMPA). The reaction involves an aryl samarium as an intermediate.

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.

Generation and Reactivities of Organocerium Reagents

Organocerium reagents, prepared in situ by the treatment of organolithium compounds with cerium(III) iodide, exhibit characteristic reactivities toward ketones; at -65 deg C, nucleophilic additions give the corresponding tertiary alcohols in excellent yields; while, at 0 deg C to ca. room temperature, reductive coupling and/or reduction of the ketones prevail.