74120-63-1

Upstream product

• 300-57-2 allylbenzene 
• 21087-29-6 trans-3-phenylprop-2-enyl chloride 
• 4392-24-9 Cinnamyl bromide 
• 768-90-1 1-Adamantyl bromide 
• 34041-44-6 1-phenylpropenyl-lithium 
• 21040-45-9 Cinnamyl acetate 
• 201230-82-2 carbon monoxide 
• 2259-30-5 tert-butylmagnesium bromide 
• 920-39-8 isopropylmagnesium bromide 
• 100-58-3 phenylmagnesium bromide 
• 507-19-7 t-butyl bromide 
• 64740-46-1 1-lithio-3-phenylpropane 
• 18292-38-1 2-methallyltrimethylsilane 
• 40595-34-4 (E)-trimethyl(3-phenylallyl)silane 

Downstream Products

• 300-57-2 allylbenzene 
• 873-66-5 1-propenylbenzene 
• 766-90-5 cis-1-phenyl-1-propylene 
• 33788-20-4 (E,Z)-1,6-diphenylhexa-1,5-diene 
• 58463-02-8 (1E,5E)-1,6-diphenyl-1,5-hexadiene 

Relevant academic research and scientific papers

Preparation of dialkoxyborylbis(bromozincio)methane and its reaction with electrophiles

Dialkoxyborylbis(bromozincio)methane was prepared from dialkoxyboryldibromomethane by the Pb-catalyzed reaction with zinc. The dialkoxyborylbis(bromozincio)methane afforded vinylboranes by TiCl4-mediated reaction with aldehydes or ketones. The

Palladium-Catalyzed Allyl-Allyl Reductive Coupling of Allylamines or Allylic Alcohols with H2as Sole Reductant

Catalytic carbon-carbon bond formation building on reductive coupling is a powerful method for the preparation of organic compounds. The identification of environmentally benign reductants is key for establishing an efficient reductive coupling reaction. Herein an efficient strategy enabling H2 as the sole reductant for the palladium-catalyzed allyl-allyl reductive coupling reaction is described. A wide range of allylamines and allylic alcohols as well as allylic ethers proceed smoothly to deliver the C-C coupling products under 1 atm of H2. Kinetic studies suggested that the dinuclear palladium species was involved in the catalytic cycle.

Single electron transfer-induced Grignard cross-coupling involving ion radicals as exclusive intermediates

The mechanism of the previously developed cross-coupling reaction of aryl Grignard reagents with aryl halides was explored in more detail. Single electron transfer from an aryl Grignard reagent to an aryl halide initiates a radical chain by giving an anion radical of the aryl halide. The following propagation cycle consists entirely of anion radical intermediates.

Palladium-catalyzed cross-coupling reactions of organogold(i) phosphanes with allylic electrophiles

Aryl and alkenylgold(i) phosphanes react regioselectively with allylic electrophiles such as cinnamyl and geranyl halides (bromide, chloride and acetates) under palladium catalysis in THF at 80 °C to afford the α-substitution product with moderate to high yields. When the reaction is performed with a chiral enantiopure secondary acetate, the α-substituted cross-coupling product is obtained with complete inversion of the stereochemistry.

Mild TiIII- and Mn/ZrIV-catalytic reductive coupling of allylic halides: Efficient synthesis of symmetric terpenes

(Chemical Equation Presented) Two new efficient methods for the regioselective homocoupling of allylic halides using either catalytic Ti III or the combination Mn/ZrIV catalyst have been developed. The regio- and stereoselectivity of the process proved to increase significantly when the Mn/ZrIV catalyst is used as the coupling reagent and when cyclic substituted allylic halides are used as substrates. The use of Lewis acids such as collidine hydrochloride allowed the quantity of catalyst to be lowered up to 0.05 equiv. We have proved the utility of these protocols with the synthesis of different terpenoids such as (+)-β-onoceradiene (1), (+)-β-onocerine (2), squalene (5), and advanced key-intermediates in the syntheses of (+)-cymbodiacetal (3) and dimeric ent-kauranoids as xindongnin M (4a).

Manganese- or iron-catalyzed homocoupling of grignard reagents using atmospheric oxygen as an oxidant

Atmospheric oxygen was used for the first time as an oxidant in metal-catalyzed homocoupling of Grignard reagents. These manganese- or iron-catalyzed reactions are efficient, cheap, and eco-friendly. They are applicable to the large-scale synthesis of symmetrical conjugated compounds. Copyright

Copper catalyzed oxidation of organozinc halides

A wide range of organozinc substrates may be oxidized in the presence of catalytic copper to give carbon-carbon bonds in high yield. The Royal Society of Chemistry 2006.

Reductive coupling of allylic esters with carbonyl compounds mediated by the mischmetall/[SmI2/Pd0cat.′] cat. system

The mischmetall/[SmI2/Pd0cat.′] cat. system has been used to mediate the allylation of ketones using a variety of allylic esters (acetates, carbonates and phosphates). Thus, a "two-stage catalysis" has been carried out using SmI2 and Pd(PPh3)4 in catalytic amounts together with mischmetall (an alloy of the light lanthanides) as a co-reductant. A catalytic scheme that takes into account previously reported reactions of SmI2/Pd 0cat. and mischmetall/SmI2,Cat. systems is proposed. It has also been shown that palladium complexes catalyse the addition of organolanthanide species to ketones. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.

Et3B-Pd-promoted allylation of benzaldehyde with allylic alcohols

In the presence of Pd(OAc)2 (0.05 equiv.) and PPh3 (0.1 equiv.), triethylborane promotes a variety of allyl alcohols to undergo allylation of benzaldehyde to provide homoallyl alcohols in good yield. (C) 2000 Elsevier Science Ltd.