112573-95-2

Upstream product

• 24808-74-0 (E)-(3-methoxybut-1-en-1-yl)benzene 
• 762-72-1 allyl-trimethyl-silane 
• 112528-83-3 trans-1-Phenyl-3-(tetrahydropyran-2-yloxy)-1-butene 
• 112528-82-2 ((E)-3-Methoxymethoxy-but-1-enyl)-benzene 
• 76987-16-1 (E)-1-Phenyl-3-<(trimethylsilyl)oxy>-1-butene 
• 79594-09-5 (E)-1-phenyl-1-<(trimethylsilyl)oxy>-2-butene 
• 36004-04-3 ethyl (E)-1-phenylbut-1-en-3-ol 
• 14371-10-9 (E)-3-phenylpropenal 
• 75-16-1 methylmagnesium bromide 
• 106-95-6 allyl bromide 
• 2622-05-1 allylmagnesium bromide 
• 51801-01-5 (E)-1-acetoxy-1-phenyl-2-butene 
• 82045-04-3 (rac)-(E)-2-acetoxy-4-phenylbut-3-ene 
• 1204403-27-9 isopropyl (E)-4-phenylbut-3-en-2-yl carbonate 

Relevant academic research and scientific papers

Nickel-catalyzed allyl-allyl coupling reactions between 1,3-dienes and allylboronates

A regiospecific allyl-allyl coupling reaction between 1,3-dienes and allylboronates has been demonstrated under nickel catalysis. Salient features of this method include the earth-abundant metal catalyst, excellent regioselectivity and good functional group tolerance. Notably, even congested allyl substrates can also be applied to this protocol, thus allowing for the rapid preparation of a series of valuable 1,5-dienes. This journal is

Catalytic stereospecific allyl-allyl cross-coupling of internal allyl electrophiles with allylB(pin)

Application of internal electrophiles in catalytic stereospecific allyl-allyl cross-coupling enable the rapid construction of multisubstituted 1,5-dienes, including those with all carbon quaternary centers. Compounds with minimal steric differentiation ca

Chemoselective and direct functionalization of methyl benzyl ethers and unsymmetrical dibenzyl ethers by using iron trichloride

Methyl and benzyl ethers are widely utilized as protected alcohols due to their chemical stability, such as the low reactivity of the methoxy and benzyloxy groups as leaving groups under nucleophilic conditions. We have established the direct azidation of chemically stable methyl and benzyl ethers derived from secondary and tertiary benzyl alcohols. The present azidation chemoselectively proceeds at the secondary or tertiary benzylic positions of methyl benzyl ethers or unsymmetrical dibenzyl ethers and is also applicable to direct allylation, alkynylation, and cyanation reactions, as well as the azidation. The present methodologies provide not only a novel chemoselectivity but also the advantage of shortened synthetic steps, due to the direct process without the deprotection of the methyl and benzyl ethers. Ethers exchanged: Methyl and benzyl ethers are chemically stable and generally tolerant under nucleophilic substitution conditions. Iron-catalyzed direct functionalizations (e.g., azidation, allylation, alkynylation, and cyanation) of methyl and benzyl ethers derived from secondary and tertiary benzyl alcohols were established with excellent regioselectivities (see scheme; PG: protecting group; Bn: benzyl; Nu: nucleophile; TMS: trimethylsilyl). Copyright

Iron-catalyzed π-activated C-O ether bond cleavage with C-C and C-H bond formation

A novel and efficient allylic alkylation reaction between π-activated ethers and allylsilane was realized under mild conditions through iron(III)-catalyzed C sp 3-O ether bond cleavage. The present protocol provides an attractive approach for the construction of sp3-sp3 C-C bonds and can be potentially applied for the selective reduction of benzyl and allyl ethers to their corresponding hydrocarbon compounds by using triethylsilane as a hydride-transfer reagent. A mild, economical, and environmentally friendly method for the construction of C sp 3-C sp 3 bonds through iron-catalyzed π-activated C-O ether bond cleavage is developed. In addition, this catalytic system can be used for the selective reduction of benzylic and allylic C-O ether bonds to C-H bonds. Copyright

Iron-Catalyzed π-Activated C-O Ether Bond Cleavage with C-C and C-H Bond Formation

A novel and efficient allylic alkylation reaction between π-activated ethers and allylsilane was realized under mild conditions through iron(III)-catalyzed C sp 3-O ether bond cleavage. The present protocol provides an attractive approach for the construction of sp3-sp3 C-C bonds and can be potentially applied for the selective reduction of benzyl and allyl ethers to their corresponding hydrocarbon compounds by using triethylsilane as a hydride-transfer reagent.

Calcium-catalyzed direct coupling of alcohols with organosilanes

A calcium-catalyzed direct substitution of π-activated alcohols with different organosilanes under very mild reaction conditions is presented. The high reactivity of the calcium catalyst allows efficient conversion of secondary and tertiary allylic, secondary benzylic, and tertiary propargylic alcohols with allyltrimethylsilane at room temperature. Furthermore, the first direct substitution of an alcohol with (E)- as well as (Z)-alkenylsilanes was achieved under mild reaction conditions. Copyright

Palladium(0) versus nickel(0) catalysis in selective functional- grouptolerant sp3-sp3 carbon-carbon bond formations

We have uncovered Pd°-catalyzed intermolecular nonsymmetrical Suzuki-Miyaura-type sp3-sp3 C-C bond formations between allyl carbonates and nontoxic allyl, allenyl, or propargyl boronates. This report represents the first use of these

Copper(II)-catalyzed allylation of propargylic and allylic alcohols by allylsilanes: a facile synthesis of 1,5-enynes

Propargylic alcohols undergo smooth deoxygenative allylation with allylsilanes in the presence of a solution of 10 mol % of copper(II) tetrafluoroborate in acetonitrile to afford the corresponding 1,5-enynes in good to high yields under mild and neutral c

Deoxygenative allylation of benzyl acetates and cinnamyl alcohols catalyzed by molecular iodine

Benzyl acetates undergo smooth deoxygenative allylation with allyltrimethylsilane in the presence of 10 mol % of molecular iodine under mild conditions to afford the corresponding allyl derivatives in excellent yields and with high selectivity. Cinnamyl alcohols also react readily with allylsilane under similar conditions. The use of molecular iodine makes this method quite simple, more convenient and cost effective. Copyright

InBr3-Catalyzed Deoxygenative Allylation of Benzylic and Allylic Alcohols and Acetates with Allyltrimethylsilane

Deoxygenative allylations of benzylic and allylic alcohols and acetates with allyltrimethylsilane in the presence of a catalytic amount of InBr3 (5 mol percent) were successfully achieved in high yields.