14310-33-9

Upstream product

• 7294-84-0 2-(2-phenylethyl)phenol 
• 74-88-4 methyl iodide 
• 74587-14-7 o-methoxybenzyl phenylacetate 
• 41398-67-8 2-phenylethynylanisole 
• 100-66-3 methoxybenzene 
• 100-42-5 styrene 
• 529-28-2 4-iodoanisol 
• 766-51-8 2-Chloroanisole 
• 103-63-9 1-phenyl-2-bromoethane 
• 578-57-4 2-bromoanisole 
• 1898-14-2 (Z)-1-(2-methoxyphenyl)-2-phenylethene 
• 536-74-3 phenylacetylene 
• 721-04-0 2-phenoxy-1-phenylethanone 
• 74587-13-6 phenylacetic o-methoxyphenylacetic anhydride 

Downstream Products

• 111088-43-8 Bis-(4-methoxy-3-phenethyl-phenyl)-iodonium; bromide 
• 111088-50-7 (S)-3-[3,5-Diiodo-4-(4-methoxy-3-phenethyl-phenoxy)-phenyl]-2-(2,2,2-trifluoro-acetylamino)-propionic acid methyl ester 
• 111087-79-7 (S)-2-Amino-3-[4-(4-hydroxy-3-phenethyl-phenoxy)-3,5-diiodo-phenyl]-propionic acid 

Relevant academic research and scientific papers

Chemoselective Hydrogenation of Alkynes to (Z) -Alkenes Using an Air-Stable Base Metal Catalyst

A highly selective hydrogenation of alkynes using an air-stable and readily available manganese catalyst has been achieved. The reaction proceeds under mild reaction conditions and tolerates various functional groups, resulting in (Z)-alkenes and allylic alcohols in high yields. Mechanistic experiments suggest that the reaction proceeds via a bifunctional activation involving metal-ligand cooperativity.

Deaminative Reductive Cross-Electrophile Couplings of Alkylpyridinium Salts and Aryl Bromides

A nickel-catalyzed reductive cross-coupling of alkylpyridinium salts and aryl bromides has been developed using Mn as the reductant. Both primary and secondary alkylpyridinium salts can be used, and high functional group and heterocycle tolerance is observed, including for protic groups. Mechanistic studies indicate the formation of an alkyl radical, and controlling its fate was key to the success of this reaction.

Catalytic Chemoselective and Stereoselective Semihydrogenation of Alkynes to E-Alkenes Using the Combination of Pd Catalyst and ZnI2

An efficient E-selective semihydrogenation of internal alkynes was developed under low dihydrogen pressure and low reaction temperature from commercially available reagents: Cl2Pd(PPh3)2, Zn0, and ZnI2. Kinetic studies and control experiments underline the significant role of ZnI2 in this process under H2 atmosphere, establishing that the transformation involves syn-hydrogenation followed by isomerization. This simple and easy-to-handle system provides a route to E-alkenes under mild conditions.

Iridium-Catalyzed Intramolecular Methoxy C?H Addition to Carbon–Carbon Triple Bonds: Direct Synthesis of 3-Substituted Benzofurans from o-Methoxyphenylalkynes

Catalytic hydroalkylation of an alkyne with methyl ether was accomplished. Intramolecular addition of the C?H bond of a methoxy group in 1-methoxy-2-(arylethynyl)benzenes across a carbon–carbon triple bond took place efficiently either in toluene at 110 °C or in p-xylene at 135 °C in the presence of an iridium catalyst. The initial 5-exo cyclization products underwent double-bond migration during the reaction to give 3-(arylmethyl)benzofurans in high yields.

Regioselective C-H alkylation of anisoles with olefins catalyzed by cationic half-sandwich rare earth alkyl complexes

A half sandwich helping: Cationic rare-earth alkyl species generated from half-sandwich rare-earth dialkyl complexes and [Ph3C][B(C 6F5)4] can serve as unique catalysts for the C-H regioselective alkylation of anisoles with alkenes. The reaction affords either ortho-monoalkylated derivatives or products substituted at the benzylic position, depending on the substrate chosen. Copyright

Nickel-mediated inter- and intramolecular reductive cross-coupling of unactivated alkyl bromides and aryl iodides at room temperature

A nickel-mediated intermolecular reductive cross-coupling reaction of unactivated alkyl bromides and aryl iodides at room temperature has been developed and successfully extended to less explored intramolecular versions and tandem cyclization-intermolecular cross-coupling. Highly stereoselective (or stereospecific) synthesis of linear-fused perhydrofuro[2,3-b]furan (pyran) and spiroketal skeletons allows rapid access to these useful building blocks, which would be potentially valuable in the synthesis of relevant natural products. A rational explanation for the formation of contiguous stereogenic centers is given. Copyright

Suzuki-miyaura cross-coupling reactions of primary alkyltrifluoroborates with aryl chlorides

(Chemical Equation Presented) Parallel microscale experimentation was used to develop general conditions for the Suzuki-Miyaura cross-coupling of diversely functionalized primary alkyltrifluoroborates with a variety of aryl chlorides. These conditions wer

Friedel-Crafts Benzylation and Phenethylation Reactions Using Benzyl and Phenethyl Benzothiazol-2-yl Carbonate Derivatives

Friedel-Crafts benzylation and phenethylation reactions of several aromatic compounds with benzyl and phenethyl benzothiazol-2-yl carbonate derivatives were carried out in the presence of scandium triflate (Sc(OTf) 3) as a catalyst. Suitable combinations of the leaving group of carbonates and acid promoters that generate cationic alkyl species were examined.

Highly active catalyst for the heterogeneous Suzuki-Miyaura reaction: Assembled complex of palladium and non-cross-linked amphiphilic polymer

An assembled insoluble catalyst, PdAS, prepared from palladium ((NH 4)2PdCl4 (1)) and non-cross-linked amphiphilic copolymer poly(N-isopropylacrylamide-co-4-diphenylstyrylphosphine) (2) was developed. It was found that PdAS is an excellent catalyst for the Suzuki-Miyaura reaction on three points: (1) The use of 8 × 10 -7 to 5 × 10-4 mol equiv of PdAS afforded the coupling products efficiently after easy workup, with the turnover number reaching up to 1 250 000. (2) The catalyst was reusable many times without loss of catalytic activity. (3) PdAS showed good stability in any reaction medium (i.e., water or aqueous or anhydrous organic solvents). Analytical study of PdAS indicates that the phosphines in 2 coordinate to palladium to form PdCl2(PPh2Ar)2 species.

Selective reduction of alkynes catalyzed by palladium acetate with sodium methoxide as the hydride source

Treatment of internal alkynes with sodium methoxide in the presence of Pd(OAc)2 and PPh3 in methanol for 48 h gave the reduction products, alkenes or alkanes in good chemical yields. This reaction proceeds through a palladium methanolate complex, followed by β-hydride elimination and reductive elimination.