92991-35-0

Upstream product

• 767-91-9 1-ethynyl-2-methoxybenzene 
• 638-45-9 1-Iodohexane 
• 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 
• 21433-45-4 1-octynyllithium 
• 31600-86-9 2-methoxyphenyllithium 

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

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

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.

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

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.

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.

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