139377-71-2

Upstream product

• 300-57-2 allylbenzene 
• 513-48-4 2-butyl iodide 
• 715-11-7 2-tosyloxybutane 
• 21087-29-6 trans-3-phenylprop-2-enyl chloride 
• 101749-61-5 tri-sec-butylindium 
• 78-76-2 s-butyl bromide 
• 109283-53-6 (E)-cinnamyloxytrimethylsilane 
• 598-30-1 sec.-butyllithium 
• 4392-24-9 Cinnamyl bromide 
• 536-74-3 phenylacetylene 
• 100-42-5 styrene 
• 105-43-1 3-methylvaleric acid 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 

Relevant academic research and scientific papers

Regioselective Single-Electron Tsuji-Trost Reaction of Allylic Alcohols: A Photoredox/Nickel Dual Catalytic Approach

A radical-mediated functionalization of allyl alcohol derived partners with a variety of alkyl 1,4-dihydropyridines via photoredox/nickel dual catalysis is described. This transformation transpires with high linear and E-selectivity, avoiding the requirement of harsh conditions (e.g., strong base, elevated temperature). Additionally, using aryl sulfinate salts as radical precursors, allyl sulfones can also be obtained. Kinetic isotope effect experiments implicated oxidative addition of the nickel catalyst to the allylic electrophile as the turnover-limiting step, supporting previous computational studies.

Iron-Catalyzed Vinylic C?H Alkylation with Alkyl Peroxides

A variety of alkyl peresters and alkyl diacyl peroxides, which are readily accessible from carboxylic acids, are utilized as general primary, secondary, and tertiary alkylating reagents for iron-catalyzed vinylic C?H alkylation of vinyl arenes, dienes, and 1,3-enynes. This transformation affords olefinic products in up to 98 % yield with high E/Z values. A broad range of functionalities, including carboxyl, boronic acid, methoxy, ester, amino, and halides, are tolerated. This protocol provides a facile approach to some olefins that are difficult to access, and hence, offers an alternative to existing systems. The synthetic utility of this method is demonstrated by late-stage functionalization of selected natural-product derivatives.

Hydroalkylation of terminal aryl alkynes with alkyl diacyl peroxides

A photo and nickel co-catalyzed hydroalkylation of terminal aryl alkynes enabled Z-preferred olefin synthesis has been developed under mild conditions. Alkyl diacyl peroxides were utilized as a new type of alkylation reagents and afforded Z-olefins as the major products in moderate to good yields.

Catalyst-controlled reverse selectivity in C-C bond formation: NHC-Cu-catalyzed α-selective allylic alkylation with organolithium reagents

An efficient and highly α-selective copper-catalyzed allylic alkylation of allylic halides with organolithium reagents is presented. The use of N-heterocyclic carbenes as ligands is key to reverse the common γ-selectivity of this transformation and gives rise to the corresponding linear products with high levels of regioselectivity.

Novel nickel-catalyzed coupling reaction of allyl ethers with chlorosilanes, alkyl tosylates, or alkyl halides promoted by vinyl-Grignard reagent leading to allylsilanes or alkenes

A new method for a carbon-silicon or carbon-carbon bond forming reaction between allyl ethers and chlorosilanes, alkyl tosylates, or alkyl halides giving rise to allylsilanes or alkenes has been developed. This reaction proceeds efficiently at ambient temperature by the combined use of nickel catalysts and a vinyl-Grignard reagent. A possible reaction pathway involving the formation of allyl-Grignard reagents via transmetallation of π-allylnickel complexes with the vinyl-Grignard reagent and subsequent trapping of the thus formed allyl-Grignard reagents with electrophiles is proposed.

Reaction of Phenyl-substituted Allyl-lithiums with Secondary Alkyl Halides. A Polar Process versus Single-electron Transfer

The reaction of 1-phenylallyl-lithium (1a) with optically active 2-halobutanes in ether in the presence of tetramethylethylenediamine or hexamethylphosphoramide gives exclusively 4-methyl-3-phenylhex-1-ene (5a) (coupling at the phenyl-substituted site) with essentially 100percent inversion of configuration.In contrast, treatment of 1,1-diphenylallyl-lithium (1b) with (-)-2-halobutanes under the same conditions results in the formation of a mixture of 4-methyl-3,3-diphenylhex-1-ene (5b) (coupling at C-1) and 4-methyl-1,1-diphenylhex-1-ene (6b) (coupling) at C-3).Moreover, C-C bond formation at the 1-position to provide (5b) is also found to proceed with complete inversionof configuration, while a small but significant loss of stereochemical integrity is observed in the case of the C-3 attack product (6b).These results suggest that a polar pathway should predominate for the formation of the C-1 attack products (5a,b), while competition between polar and single-electron-transfer processes occurs for the formation of the C-3 attack product (6b).