74333-46-3

Upstream product

• 34713-70-7 2-Phenylpropanal 
• 2622-05-1 allylmagnesium bromide 
• 24850-33-7 allyltributylstanane 
• 762-73-2 trimethyl(allyl)stannane 
• 75863-14-8 2-Propenyltitanium triisopropoxide 
• 53317-08-1 allyl-9-borabicyclo<3.3.1>nonane 
• 762-72-1 allyl-trimethyl-silane 
• 1730-25-2 allylmagnesium bromide 
• 114634-03-6 2-Phenyl-1-trimethylsilanyl-propan-1-one 
• 754-56-3 3-(tert-butyl)-2,2-dimethylhex-5-en-3-ol 
• 6728-21-8 allyl mesylate 
• 141-82-2 malonic acid 
• 7393-43-3 tetraallyl tin 
• 4436-22-0 (2S,3R)-2-methyl-3-phenyloxirane 

Relevant academic research and scientific papers

A Mechanochemical Zinc-Mediated Barbier-Type Allylation Reaction under Ball-Milling Conditions

A ball-milling-enabled zinc-mediated Barbier-type allylation reaction is reported. Notably, running the reaction in this manner renders it effective irrespective of the initial morphology of the zinc metal. The process is operationally simple, does not re

Allylation of aldehydes by dual photoredox and nickel catalysis

Here we report the application of dual nickel/photoredox catalysis to the allylation of aliphatic, aromatic and heteroaromatic aldehydes by using commercially available reagents. The process utilizes the combination of a Ni(ii) complex, [Ru(bpy)3]2+ as a photoredox catalyst, and allylacetate under blue LED irradiation, and allows the synthesis of a large variety of homoallylic alcohols.

NHC-Copper-Catalyzed Tandem Hydrocupration and Allylation of Alkenyl Boronates

A tandem hydrocupration/allylation of alkenyl boronates efficiently proceeds with NHC-copper catalysts using hydrosilane and allyl phosphate as reagents. In the presence of IMes-Cu catalyst, the allylation of in situ generated Β-α-copper intermediates smoothly occurs to give homoallylic boronates in high yields, despite competitive side reaction pathways. Mono- and disubstituted alkenyl boronates were effective in the reaction with terminal allyl phosphates, but trisubstituted substrates showed limited reactivity.

Ti/Pd bimetallic systems for the efficient allylation of carbonyl compounds and homocoupling reactions

The allylation, crotylation and prenylation of aldehydes and ketones with stable and easily handled allylic carbonates is promoted by a Ti/Pd catalytic system. This Ti/Pd bimetallic system is especially convenient for the allylation of ketones, which are infrequent substrates in other related protocols, and can be carried out intramolecularly to yield five- and six-membered cyclic products with good stereoselectivities. In addition, Ti/Pd-mediated reductions and Wuertz-type dimerisation reactions can be readily carried out from allyl carbonates and carboxylates.

Ti-catalyzed Barbier-type allylations and related reactions

Titanocene(III) complexes, easily generated in situ from commercial Ti IV precursors, catalyze Barbiertype allylations, intramolecular crotylations (cyclizations), and prenylations of a wide range of aldehydes and ketones. The reaction displays surprising and unprecedented mechanistic subtleties. In cyclizations a fast and irreversible addition of an allyl radical to a TiIII-coordinated carbonyl group seems to occur. Intermolecular additions to conjugated aldehydes proceed through a coupling of a Ti IV-bound ketyl radical with an allyl radical. Reactions of ketones with allylic halides take place by the classical addition of an allylic organometallic reagent. The radical coupling processes enable transformations such as the highly regioselective α-prenylation that are otherwise difficult to achieve. The mild reaction conditions and the possibility to employ titanocene complexes in only catalytic quantities are highly attractive features of our protocol. These unusual properties have been taken advantage of for the straightforward synthesis of the natural products rosiridol, shikalkin, and 12-hydroxysqualene.

Carbonyl allylations by 3-halopropenes or 2-propenyl mesylate with tin(IV) chloride and tetrabutylammonium iodide

2-Propenyl tin species, prepared from 3-halopropenes or 2-propenyl mesylate with tin(IV) chloride and tetrabutylammonium iodide in dichloromethane, causes nucleophilic addition to aldehydes to produce the corresponding homoallylic alcohols.

NbCl5: A novel Lewis acid in allylation reactions

Allylation reactions promoted by niobium pentachloride are described. Allylstannanes were added to aromatic and aliphatic aldehydes and aromatic imines in good yields. Excellent syn diastereoselectivities were obtained in the addition of (E)-cinnamylstannane to benzaldehyde (49:1) and in the addition of crotylstannane to N-benzylideneaniline (46:1).

Preparation and reactions of water stable hypervalent 10-Sn-5 allyl ate complexes

Hypervalent 10-Sn-5 allyl and crotyl tin ate complexes bearing Martin ligands were prepared and found to be surprisingly stable in water. These compounds were found to react with aldehydes in the presence of weak Lewis acids such as LiBr to give the corresponding homoallyl alcohols. Product analysis of the reaction of the crotyl compounds indicated that the reaction occurred via a cyclic transition state unlike an acyclic transition state operative for widely utilized allyltrialkyltin reagents that are of ordinary valency.

Stereoselective addition of organomanganese reagents to chiral acylsilanes and aldehydes

Organomanganese halides and organomanganates prepared by transmetalation of organolithium and Grignard reagents add smoothly to the carbonyl moiety of acylsilanes and of substituted aldehydes bearing a chiral center at the α-position affording the desired

Niobium(V) chloride-mediated allylation of aldehydes. Scope and stereoselectivity

Niobium chloride promoted the addition of allylstannanes to aromatic and aliphatic aldehydes. Excellent syn diastereoselectivity was obtained in the addition of E-cinnamylstannane to benzaldehyde (49:1). In the addition of allylstannane to racemic 2-phenylpropionaldehyde, syn diastereoselection (Cram-anti-Cram = 3:1) was observed. The same level of diastereoselection was achieved in the reaction between crotylstannane and benzaldehyde.