92991-35-0

Upstream product

• 767-91-9 1-ethynyl-2-methoxybenzene 
• 638-45-9 1-Iodohexane 
• 21433-45-4 1-octynyllithium 
• 31600-86-9 2-methoxyphenyllithium 
• 578-57-4 2-bromoanisole 
• 629-05-0 n-octyne 
• 529-28-2 4-iodoanisol 
• 766-51-8 2-Chloroanisole 
• 109-72-8 n-butyllithium 

Downstream Products

• 104971-01-9 1-((E)-1-Iodo-oct-1-enyl)-2-methoxy-benzene 
• 104971-00-8 (Z)-1-(2-hydroxyphenyl)-2-phenylthio-oct-1-ene 

Relevant academic research and scientific papers

Suzuki-Miyaura coupling of alkynylboronic esters generated in situ from acetylenic derivatives

(equation presented) A new effective Suzuki-Miyaura coupling reaction between alkynylboronic esters (generated in situ from acetylenic derivatives) and arylbromides or vinylbromides is reported.

A Metal-Free Route to Heterocyclic Trifluoromethyl- and Fluoroalkylselenolated Molecules

A metal-free methodology to easily synthesize various CF3Se-containing heterocyclic compounds has been developed through intramolecular ring closures of alkynes promoted with CF3SeCl. Moreover, this strategy has also been extended to other fluoroalkylselenyl groups.

Palladium-catalyzed coupling of aryl halides with alkynes

A method is provided to couple an aryl halide to an alkyne comprising reacting a compound of the formula ArX, wherein Ar is a substituted or unsubstituted aryl group and X is I or Br, with a compound of the formula HC≡C—R1 wherein R1 /sup

Efficient suzuki-miyaura coupling reactions between lithium alkynyltrimethylborates and aryl chlorides

The Pd-catalysed alkynylation of alkynylboronic esters (generated in situ) with various aryl chlorides in the presence of Pd2(dba)3, the sterically hindered dihydroimidazolium salt 4 as the precatalyst and CsF is reported. Under thes

Palladium-catalyzed suzuki coupling with terminal alkynes - Application to the synthesis of 2,3-disubstituted benzo[b]furans

The Suzuki coupling reaction between alkynylboronic esters (generated in situ from acetylenic derivatives) and aryl bromides, pyridyl bromides or vinyl bromides is reported. 5-endo-dig-iodocyclisation of o-alkynylanisoles, generated by this palladium-catalyzed Suzuki coupling reaction, was performed with N-iodosuccinimide (NIS) in the presence of BCl3. 2-Substituted 3-iodobenzo[b]furans were synthesized and transformed into 2,3-disubstituted benzo[b]furans by Suzuki coupling reactions in high yields. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.

Synthesis of 2,3-disubstituted benzo[b]furans by the palladium-catalyzed coupling of o-iodoanisoles and terminal alkynes, followed by electrophilic cyclization

2,3-Disubstituted benzo[b]furans are readily prepared under very mild reaction conditions by the palladium/copper-catalyzed cross-coupling of various o-iodoanisoles and terminal alkynes, followed by electrophilic cyclization with I2, PhSeCl, Or

Ligand-, copper-, and amine-free sonogashira reaction of aryl iodides and bromides with terminal alkynes

Conditions for an efficient ligand-, copper-, and amine-free palladium-catalyzed Sonogashira reaction of aryl iodides and bromides with terminal alkynes have been developed. Critical to the success of this new protocol is the use of tetrabutylammonium ace

Sonogashira coupling using bulky palladium-phenanthryl imidazolium carbene catalysis

(Matrix presented) Bulky phenanthracenyl imidazolium-derived carbene ligands were investigated for copper-free Sonogashira coupling with terminal acetylenes. Aryl bromides and iodides gave coupled products in excellent yields from the Pd(PPh3)2Cl2 complex with potassium t-butoxide and 18-crown-6 in THF. A remarkable dependence on the size of the ligand was found. The highest yields were obtained with the bulky 2,9-dicyclohexyl-10-phenanthryl ligand 5.

Efficient Palladium-Catalyzed Coupling of Aryl Chlorides and Tosylates with Terminal Alkynes: Use of a Copper Cocatalyst Inhibits the Reaction

Less catalyst, lower temperature, and greater generality are the advantages of the new general protocol over those previously described for the palladium-catalyzed coupling of aryl chlorides and alkynes (see scheme). Better results are obtained without a copper cocatalyst, which has been found to inhibit product formation in the coupling reaction of aryl chlorides with terminal alkynes.

Highly satisfactory procedures for the Pd-catalyzed cross coupling of aryl electrophiles with in situ generated alkynylzinc derivatives.

[reaction: see text] Two new and very efficient procedures (Procedures A and B) are reported for the Pd-catalyzed cross coupling of aryl electrophiles with terminal alkynes via their in situ conversion into alkynylzinc derivatives. Procedure A is particul