4957-17-9

Upstream product

• 100-66-3 methoxybenzene 
• 83036-58-2 prenyl diisopropyl phosphate 
• 870-63-3 prenyl bromide 
• 74-88-4 methyl iodide 
• 108-95-2 phenol 
• 78-79-5 isoprene 
• 40904-92-5 4-(2'-methoxyphenyl)-2-methyl-3-butyn-2-ol 
• 556-82-1 3-methyl-2-buten-1-ol 
• 529-28-2 4-iodoanisol 
• 141550-13-2 4,4,5,5-tetramethyl-2-(3-methylbut-2-enyl)-1,3,2-dioxaborolane 
• 33567-59-8 (2-methoxy-phenyl)-acetaldehyde 
• 24470-78-8 isopropyltriphenylphosphonium iodide 
• 638-10-8 ethyl 3-methylbut-2-enoate 
• 578-57-4 2-bromoanisole 

Downstream Products

• 99347-59-8 [2-Chloro-3-(2-methoxy-phenyl)-1,1-dimethyl-propylsulfanyl]-acetic acid methyl ester 
• 99347-49-6 [2-Chloro-1-(2-methoxy-benzyl)-2-methyl-propylsulfanyl]-acetic acid methyl ester 
• 99347-79-2 1-(2-Chloro-3-methyl-but-3-enyl)-2-methoxy-benzene 
• 79699-55-1 1,1-dimethyl-4-methoxyindan 
• 91969-55-0 4-hydroxy-1,1-dimethylindane 
• 99347-70-3 3-carbomethoxymethylthio-4-(2-methoxyphenyl)-2-methyl-1-butene 
• 99347-93-0 (E)-6-(2-Methoxy-phenyl)-4-methyl-hex-4-enoic acid methyl ester 

Relevant academic research and scientific papers

Synthesis of Tetrahydroisoindolinones via a Metal-Free Dehydrogenative Diels-Alder Reaction

A metal-free dehydrogenative Diels-Alder reaction of substituted alkenes for the synthesis of tetrahydroisoindolinones has been exploited for the first time. This new method features functional group tolerance and broad substrate scope, providing an efficient access to biologically active tetrahydroisoindolinone skeletons with endo steroselectivity in good to excellent yields. (Figure presented.).

Metal-Free Dehydrogenative Diels-Alder Reactions of Prenyl Derivatives with Dienophiles via a Thermal Reversible Process

An efficient dehydrogenative Diels-Alder reaction of prenyl derivatives with dienophiles has been developed. The reaction exhibits broad substrate scope and provides efficient access to cyclohexene derivatives with good to excellent yields. A reasonable mechanism involving a metal-free thermal reversible process is proposed.

Nickel-Catalyzed Regioselective Reductive Cross-Coupling of Aryl Halides with Polysubstituted Allyl Halides in the Presence of Imidazolium Salts

The nickel-catalyzed direct reductive cross-coupling of aryl halides with readily accessible polysubstituted allyl halides provides an efficient method for preparing diverse allylated arenes under mild conditions. Both allyl bromides and allyl chlorides are compatible with the transformation.

Copper-free arylation of 3,3-disubstituted allylic halides with triazene-softened aryl Grignard reagents

A copper-free allylic arylation reaction between 3,3-disubstituted allylic halides and triazene-softened aryl Grignard reagents has been developed. This protocol presents a direct and efficient way to construct both α- or γ-isomers with high regioselectivity under environmentally benign conditions. Various functional groups can be tolerated in the reaction and the products are of high value for multiple synthetic applications. The α- and γ-isomers can be converted to the corresponding 3H-indole and indole derivatives in multigram scale respectively.

A surprising substituent effect provides a superior boronic acid catalyst for mild and metal-free direct Friedel-Crafts alkylations and prenylations of neutral arenes

The development of more general and efficient catalytic processes for Friedel-Crafts alkylations is an important objective of interest toward the production of pharmaceuticals and commodity chemicals. Herein, 2,3,4,5-tetrafluorophenylboronic acid was identified as a potent air- and moisture-tolerant metal-free catalyst that significantly improves the scope of direct Friedel-Crafts alkylations of a variety of slightly activated and neutral arenes, including polyarenes, with allylic and benzylic alcohols. This method also provides a simple alternative for the direct installation of prenyl units commonly found in naturally occurring arenes. Alkylations with benzylic alcohols occur under exceptionally mild conditions.

Regioselective cross-coupling of allylboronic acid pinacol ester derivatives with aryl halides via Pd-PEPPSI-IPent

The cross-coupling reactions of allylboronic acid pinacol ester derivatives with aryl and heteroaryl halides occurred with high selectivity (>97%) at the α-carbon of the allylboron reagent in the presence of Pd-PEPPSI-IPent precatalyst and 5 M KOH in refluxing THF. In the case of trisubstituted allylboronates with different substituents on the olefin, minor olefin geometry isomerization was observed (E/Z & 80/20).

Introduction of allyi and prenyl side-chains into aromatic systems by suzuki cross-coupling reactions

This paper reports some studies aiming at the developement of a general protocol useful for the synthesis of allyl- and prenylaromatic compounds. The first part deals with, the preparation of boron reagents like arylboronic acids and their pinacol esters as well as of pinacol allyl- and prenylboronates. The second part of the paper is devoted to the use of these boron reagents in Suzuki-Miyaura cross-coupling reactions leading to allylation and prenylation of aromatic compounds. Of the six methods studied, the most promising re-suits were obtained by using the Pd2(dba)3-catalyzed reactions of arylboronic acids with allyl and prenyl bromides, that lead to the products of cross coupling in high yields (average 87%), and the reactions of aryl trifluoroborates with allyl and prenyl bromides catalyzed by Pd(OAc)2 that lead to the products of coupling in all cases in high yields (average 82%).

Versatile friedel-crafts-type alkylation of benzene derivatives using a molybdenum complex/ortho-chloranil catalytic system

A variety of molybdenum complexes catalyze Friedel-Crafts-type alkylation reactions of benzene derivatives with alkenes and alcohols in the presence of an organic oxidant, o-chloranil. The utilization of [Mo(CO)6] and two equivalents of o-chloranil catalytically furnished the hydroarylation product of norbornene with p-xylene at 80°C, whereas [Cr(CO)6] and [W(CO)6] failed to catalyze the same reaction, thus indicating the importance of the molybdenum source. The best results were obtained when a molybdenum(II) complex [CpMoCl(CO)3] (Cp = cyclopentadienyl) was used as a precatalyst. The hydroarylation reactions also took place with styrenes, cyclohexenes, and 1 -hexene as olefin substrates. The electrophilic-substitution mechanism was proposed on the basis of the ortho/para selectivities and the Markovnikov selectivities observed for the hydroarylation products. Our hypothesis was further corroborated by the fact that in the presence of the [CpMoCl(CO)3]/o-chloranil catalytic system, secondary, benzylic, or allylic alcohols participated in the alkylation of benzenes with similar selectivities.

Synthesis of 1,1-dimethyl-4-indanol derivatives

The synthesis of 1,1-dimethyl-4-indanols (3a,b) has been achieved by intramolecular Friedel-Crafts cyclization of 2-(3-methyl-2-butenyl)phenols (5a,b) or 1-methoxy-2-(3-methyl-2-butenyl)benzenes (6a,b) followed by demethylation, respectively. It was found that the solvent was critical for the formation of different products in the intramolecular Friedel-Crafts reactions of 6. The unexpected product 4-methoxy-1,1,6,6-tetramethyl-as-hydrindacene (11) was obtained from the Friedel-Crafts reactions of 6a and its structure was confirmed by X-ray diffraction analysis. The key intermediates 5a,b were prepared by ortho-alkenylation of phenols with 1-bromo-3-methyl-2-butene, and the reaction temperature exerted an obvious impact on the yield of 2-(3-methyl-2-butenyl)phenol (5a). Copyright Taylor & Francis Group, LLC.

Reaction between phenols and isoprene under zeolite catalysis. Highly selective synthesis of chromans and o-isopentenylphenols

Chromans 3 and o-isopentenylphenols 4 are synthesized in satisfactory to good yields and selectivities by the reaction of phenols and isoprene in the presence of the commercially available acid faujasite zeolite HSZ-360.