312708-99-9

Upstream product

• 95-46-5 2-methylphenyl bromide 
• 629-05-0 n-octyne 
• 615-37-2 ortho-methylphenyl iodide 
• 95-49-8 2-methylchlorobenzene 
• 21433-45-4 1-octynyllithium 
• 54663-78-4 tributyl(thien-2-yl)stannane 
• 5097-05-2 2,2′-sulfinylbis(methylbenzene) 

Downstream Products

• 1243000-86-3 (Z)-1-iodo-1-(2-methylphenyl)-2-phenylmethyl-1-octene 
• 1243000-84-1 C₂₂H₂₇⁽²⁾H 
• 1243000-65-8 (E)-1-(2-methylphenyl)-2-phenylmethyl-1-octene 
• 1446486-58-3 2-hexyl-3-o-tolylbenzofuran 

Relevant academic research and scientific papers

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.

Binuclear Pd(I)-Pd(I) Catalysis Assisted by Iodide Ligands for Selective Hydroformylation of Alkenes and Alkynes

Since its discovery in 1938, hydroformylation has been thoroughly investigated and broadly applied in industry (>107 metric ton yearly). However, the ability to precisely control its regioselectivity with well-established Rh- or Co-catalysts has thus far proven elusive, thereby limiting access to many synthetically valuable aldehydes. Pd-catalysts represent an appealing alternative, yet their use remains sparse due to undesired side-processes. Here, we report a highly selective and exceptionally active catalyst system that is driven by a novel activation strategy and features a unique Pd(I)-Pd(I) mechanism, involving an iodide-assisted binuclear step to release the product. This method enables β-selective hydroformylation of a large range of alkenes and alkynes, including sensitive starting materials. Its utility is demonstrated in the synthesis of antiobesity drug Rimonabant and anti-HIV agent PNU-32945. In a broader context, the new mechanistic understanding enables the development of other carbonylation reactions of high importance to chemical industry.

Iron(III)-Catalyzed Hydration of Unactivated Internal Alkynes in Weak Acidic Medium, under Lewis Acid-Assisted Br?nsted Acid Catalysis

Alkylarylalkynes are converted with full regioselectivity into the corresponding arylketones by formal hydration of the triple bond under weak acidic conditions, at times and temperatures (≤95 °C) comparable to those used for terminal alkynes. The process catalyzed by Fe2(SO4)3nH2O in glacial acetic acid exhibits good functional group compatibility, including that with bulky triple bond substituents, and can be extended to the one-pot transformation of aryltrimethylsilylacetylenes into acetyl derivatives via a desilylation-hydration sequence. The overall reactivity pattern along with proton affinity data indicate that the triple bond is activated by proton transfer rather than by π-interaction with the metal ion. This mechanistic feature, at variance with that of noble metal catalysts, accounts for the total regioselectivity and the insensitivity to steric hindrance exhibited by the Fe2(SO4)3nH2O/AcOH catalytic system. (Figure presented.).

C-S Bond Alkynylation of Diaryl Sulfoxides with Terminal Alkynes by Means of a Palladium-NHC Catalyst

Sonogashira-Hagihara-type alkynylation of diaryl sulfoxides with unactivated terminal alkynes has been developed. With a combination of a palladium-NHC catalyst and LiO t Bu as a base, a series of diaryl sulfoxides were converted into the alkynylated products via C-S bond cleavage.

Stereo-defined synthesis of differentially all-carbon tetrasubstituted alkenes derived from (E)-1-bromo-2-iodoalkenes

An intuitive approach to differentially all-carbon tetrasubstituted olefins from a scaffold of (E)-1-bromo-2-iodoalkenes is described. The iodine atom of the scaffold selectively undertook CuTC-mediated cross-coupling reactions with organotin reagents, suppressing a side-reaction of β-halogen elimination. The resultant vinyl bromides were successfully subjected to various transformations into tetrasubstituted olefins bearing four different carbon-linked groups. The crystallographic analysis revealed that the configuration of the double bonds is fully retained in those two steps. Thus, the template strategy would provide a new entry for preparing stereo-defined tetrasubstituted alkenes.

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 iron/copper cocatalyzed alkynylation of aryl iodides with terminal alkynes

(Equation Presented) We developed a highly efficient and practical protocol for the coupling of terminal alkynes with aryl iodides that is catalyzed by inexpensive and environmentally benign Fe/Cu. A broad spectrum of substrates can participate in the process effectively to produce desired products in good yields. The versatility, generality, low cost, and environmental friendliness, in combination with exceptionally high reaction rates, render this method particularly attractive for industrial applications.

Cp*Li as a base: application to palladium-catalyzed cross-coupling reaction of aryl-X or alkenyl-X (X=I, Br, OTf, ONf) with terminal acetylenes

The reaction of aryl-X or alkenyl-X (X=I, Br, OTf, ONf) with terminal acetylenes in the presence of a catalytic amount of Pd(OAc)2 provided the alkynylated products in good yields by using Cp*Li (Cp*=1,2,3,4,5-pentamethylcyclopentadienyl) as a base.

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

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