87331-35-9

Upstream product

• 106-38-7 para-bromotoluene 
• 17488-65-2 4-phenylbut-3-en-2-ol 
• 52755-38-1 1-phenyl-2-buten-1-ol 
• 5720-05-8 4-methylphenylboronic acid 
• 100-42-5 styrene 
• 536-50-5 CH₃C₆H₄CH(CH₃)OH 
• 624-31-7 4-tolyl iodide 
• 1356467-99-6 4-(boronic acid pinacolate ester)-4-phenyl-2-butene 

Relevant academic research and scientific papers

Synthesis of internal olefins by direct coupling of alcohols and olefins over MoΒ zeolite

An efficient and novel Moβ zeolite catalyzed sp2-sp3 C–C bond development reaction over the direct coupling of alcohols and alkenes has been performed in solvent free environment. The current method gives an attractive access to a wide variety of polysubstituted alkenes in good to excellent yields. The Moβ zeolite was effectively reused for up to 5 successive cycles.

Transition-Metal-Free Sulfuration/Annulation of Alkenes: Economical Access to Thiophenes Enabled by the Cleavage of Multiple C-H Bonds

A novel, atom economical, and transition-metal-free strategy for the synthesis of thiophenes from substituted buta-1-enes with potassium sulfide has been presented. The reaction achieves double C-S bond formations via cleavage of multiple C-H bonds and provides an efficient approach to access various functionalized thiophenes. Moreover, the strategy can also be used for the synthesis of thiophenes from 1,4-diaryl-1,3-dienes. Mechanistically, DMSO plays a role of oxidant and S3?- in situ generated from K2S is involved.

Dual nickel and Lewis acid catalysis for cross-electrophile coupling: The allylation of aryl halides with allylic alcohols

Controlling the selectivity in cross-electrophile coupling reactions is a significant challenge, particularly when one electrophile is much more reactive. We report a general and practical strategy to address this problem in the reaction between reactive and unreactive electrophiles by a combination of nickel and Lewis acid catalysis. This strategy is used for the coupling of aryl halides with allylic alcohols to form linear allylarenes selectively. The reaction tolerates a wide range of functional groups (e.g. silanes, boronates, anilines, esters, alcohols, and various heterocycles) and works with various allylic alcohols. Complementary to most current routes for the C3 allylation of an unprotected indole, this method provides access to C2 and C4-C7 allylated indoles. Preliminary mechanistic experiments reveal that the reaction might start with an aryl nickel intermediate, which then reacts with Lewis acid activated allylic alcohols in the presence of Mn.

A novel efficient method for the synthesis of substituted olefins; Cross coupling of two different alcohols using NaHSO4/SiO2

Simple and efficient cross coupling of alcohols was developed in the presence of NaHSO4/SiO2 to give the corresponding substituted olefins. Direct coupling of alcohols and alkenes was also achieved to give substituted olefins. NaHSO4/SiO2 could be recycled 7 times without loss of catalytic activity.

Suzuki-Miyaura cross-couplings of secondary allylic boronic esters

Palladium-catalyzed cross-coupling reactions of secondary allylic boronic esters with iodoarenes were demonstrated under the conditions previously described for the coupling of benzylic substrates. The regioselectivity of the process was largely dictated by the pattern of olefin substitution. The Royal Society of Chemistry 2012.