24808-74-0

Upstream product

• 67-56-1 methanol 
• 17488-65-2 4-phenylbut-3-en-2-ol 
• 1515-78-2 buta-1,3-dien-1-ylbenzene 
• 82045-04-3 (rac)-(E)-2-acetoxy-4-phenylbut-3-ene 
• 14371-10-9 (E)-3-phenylpropenal 
• 557-20-0 diethylzinc 
• 4364-06-1 (E)-cinnamaldehyde dimethylacetal 
• 75-16-1 methylmagnesium bromide 
• 1896-62-4 (E)-benzalacetone 
• 14289-95-3 (E)-(3-isopropoxyprop-1-en-1-yl)benzene 
• 1476-07-9 (E)-(3-ethoxy-1-propen-1-yl)benzene 
• 21087-29-6 trans-3-phenylprop-2-enyl chloride 
• 82859-39-0 trans-cinnamyl iodide 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 

Downstream Products

• 169694-34-2 (3-methyl-1,5-hexadien-1-yl)-benzene 
• 73222-65-8 1-methyl-3-phenylhexa-1,5-diene 
• 74608-23-4 4-methyl-N-(4-phenylbut-3-en-2-yl)benzenesulfonamide 
• 106728-00-1 (E)-1,3-diphenyl-1-oxo-4-hexene 
• 106728-01-2 (E)-1,5-diphenyl-3-methyl-1-oxo-4-pentene 
• 112528-89-9 [(E)-1-(2-Methyl-allyl)-but-2-enyl]-benzene 
• 112528-88-8 ((E)-3,5-Dimethyl-hexa-1,5-dienyl)-benzene 
• 101266-90-4 (E)-(3-propoxybut-1-enyl)benzene 
• 112528-98-0 (E)-(±)-2-methyl-4-phenylbut-3-enenitrile 
• 1896-62-4 (E)-benzalacetone 
• 7302-00-3 (E)-1,3-diphenyl-1-butene 
• 144789-20-8 (E)-1-phenyl-3(S)-(trimethylsilyl)-1-butene 
• 233672-89-4 3-phenyl-1-methyl-prop-2-en-1-azide 

Relevant academic research and scientific papers

Allylic Substitution Catalyzed by a New Molybdenum Complex

A new molybdenum(II) complex (E), generated in situ from Mo(CO)6 by sequential treatment with PhCH2(Et)3N+Cl- and CF3SO3Ag (3 equiv.), has been found to catalyze the substitution of allylic acetates with MeOH (4 -> 5 8; 9

Nickel-Catalyzed Arylation of C(sp3)-O Bonds in Allylic Alkyl Ethers with Organoboron Compounds

A nickel-catalyzed cross-coupling of allylic alkyl ethers with organoboron compounds through the cleavage of the inert C(sp3)-O(alkyl) bonds is described. Several types of allylic alkyl ethers can be coupled with various boronic acids or their derivatives to give the corresponding products in good to excellent yields with wide functional group tolerance and excellent regioselectivity. The gram-scale reaction and late-stage modification of biologically active compounds further prove the practicality of this synthetic method.

Nickel-Mediated Enantiospecific Silylation via Benzylic C-OMe Bond Cleavage

Benzylic stereocenters are found in bioactive and drug molecules, as enantiopure benzylic alcohols have been used to build such a stereogenic center, but are limited to the construction of a C-C bond. Silylation of alkyl alcohols has the potential to build bioactive molecules and building blocks; however, the development of such a process is challenging and unknown. Herein, we describe an unprecedented AgF-assisted nickel catalysis in the enantiospecific silylation of benzylic ethers.

Stereoselective synthesis of allyl ethers using α,β-unsaturated acylsilanes

The reaction behavior of silylvinylmethanols with acid catalysts was investigated. The starting silylvinylmethanols 2 were prepared by the reaction of the corresponding α,β-unsaturated acylsilanes 1 with organocerium reagents. The reaction of 2 with TsOH

Oxidative cleavage of allyl ethers by an oxoammonium salt

A method to oxidatively cleave allyl ethers to their corresponding aldehydes mediated by an oxoammonium salt is described. Using a biphasic solvent system and mild heating, cleavage proceeds readily, furnishing a variety of α,β-unsaturated aldehydes and ketones.

Pincer-Nickel-Catalyzed Allyl-Aryl Coupling between Allyl Methyl Ethers and Arylzinc Chlorides

The P,N,N-pincer nickel complex [Ni(Cl){N(2-Ph2PC6H4)(2′-Me2NC6H4)}]-catalyzed allyl-aryl coupling was studied. The reaction of allyl methyl ethers, including (1-methoxyallyl)arenes and (3-methoxyprop-1-en-1-yl)arenes, with arylzinc chlorides afforded linear (E)-alkenes in high yields, whereas the reaction of (E)-1-methoxytridec-2-ene with p-Me2NC6H4ZnCl generated a mixture of linear and branched alkenes.

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

Efficient assembly of α-aryl and α-vinyl nitriles via iron-catalyzed ether bond activation

A novel and practical method for the synthesis of diverse α-aryl and α-vinyl nitriles was developed via an iron-catalyzed sp3 C-O ether bond cleavage with C-C bond formation in the reaction of π-activated ethers with TMSCN.

Efficient assembly of α-aryl and α-vinyl nitriles via iron-catalyzed ether bond activation

A novel and practical method for the synthesis of diverse α-aryl and α-vinyl nitriles was developed via an iron-catalyzed sp3 C-O ether bond cleavage with C-C bond formation in the reaction of π-activated ethers with TMSCN.

Iron-catalyzed N-alkylation using π-activated ethers as electrophiles

A new method for the synthesis of diverse N-alkylation compounds was developed via an iron-catalyzed etheric Csp3-O cleavage with the C-N bond formation in the reaction of π-activated ethers with various nitrogen-based nucleophiles. In addition, the mechanism of this reaction was investigated. The Royal Society of Chemistry 2013.