69790-20-1

Upstream product

• 100-42-5 styrene 
• 1629-58-9 4-penten-3-one 
• 2270-20-4 5-Phenylpentanoic acid 
• 79-03-8 propionyl chloride 
• 27152-04-1 (4-phenylbutyl)magnesium bromide 
• 925-90-6 ethylmagnesium bromide 
• 80473-65-0 dilithium divinylcyanocuprate 

Downstream Products

• 60012-63-7 7-phenylheptan-3-ol 
• 622-21-9 dicinnamylideneacetone 

Relevant academic research and scientific papers

Hemilabile Benzyl Ether Enables Γ-C(sp3)-H Carbonylation and Olefination of Alcohols

Pd-catalyzed C(sp3)-H activation of alcohol typically shows β-selectivity due to the required distance between the chelating atom in the attached directing group and the targeted C-H bonds. Herein we report the design of a hemilabile directing group which exploits the chelation of a readily removable benzyl ether moiety to direct Γ- or δ-C-H carbonylation and olefination of alcohols. The utility of this approach is also demonstrated in the late-stage C-H functionalization of β-estradiol to rapidly prepare desired analogues that required multi-step syntheses with classical methods.

Hemilabile Benzyl Ether Enables γ-C(sp3)-H Carbonylation and Olefination of Alcohols

Pd-catalyzed C(sp3)-H activation of alcohol typically shows β-selectivity due to the required distance between the chelating atom in the attached directing group and the targeted C-H bonds. Herein we report the design of a hemilabile directing group which exploits the chelation of a readily removable benzyl ether moiety to direct γ- or δ-C-H carbonylation and olefination of alcohols. The utility of this approach is also demonstrated in the late-stage C-H functionalization of β-estradiol to rapidly prepare desired analogues that required multi-step syntheses with classical methods.

Iminyl Radical-Triggered Intermolecular Distal C(sp3)-H Heteroarylation via 1,5-Hydrogen-Atom Transfer (HAT) Cascade

An efficient iron-catalyzed intermolecular remote C(sp3)-H heteroarylation of alkyl ketones has been developed via an iminyl radical-triggered 1,5-hydrogen-atom transfer (HAT) cascade. This protocol was amenable to a wide variety of alkyl ketones and heteroaryls, thus providing a straightforward method for the late-stage functionalization of alkylketones and heteroaryls.

Reactions of acylzirconocene chloride with nucleophiles: Bimodal reactivity at β- and acyl carbons of α,β-unsaturated acylzirconocene chloride

Reactions of α,β-unsaturated acylzirconocene chloride with nucleophiles showed novel bimodal reactivity at the β- and acyl carbons depending upon the nucleophile employed, and the formation of ketone α,β-dianionic species was also observed. (C) 2000 Elsev

Diazo decomposition in the presence of tributyltin hydride. Reduction of α-diazo carbonyl compounds

The diazo group of a series of α-diazo carbonyl compounds can be reduced to the corresponding CH2 group by Bu3SnH under Cu(acac)2-catalytic or photochemical conditions. The mechanistic aspects of this reaction were investigated in some detail, and a possible reaction pathway was discussed. (C) 2000 Elsevier Science Ltd.

B-alkylcatecholboranes as a source of radicals for efficient conjugate additions to unsaturated ketones and aldehydes

Selective and efficient generation of alkyl radicals from alkenes as well as their addition to unsaturated ketones and aldehydes is reported. The method is based on a simple one-pot procedure involving the hydroboration of the alkene with catecholborane, followed by treatment with a catalytic amount of oxygen in the presence of DMPU and a radical trap. Examples of cyclization and cascade reactions are reported.