21148-30-1

Upstream product

• 16519-25-8 (E)-cinnamyl phenyl ether 
• 2657-25-2 (E)-1-(4-hydroxyphenyl)-3-phenylprop-2-en-1-one 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 108-95-2 phenol 
• 21040-45-9 Cinnamyl acetate 
• 4393-06-0 1-Phenyl-2-propen-1-ol 
• 444575-79-5 carbonic acid 1,1-dimethylethyl 1-phenyl-2-propenyl ester 
• 100-52-7 benzaldehyde 
• 71597-85-8 (p-hydroxyphenyl)boronic acid 
• 87802-71-9 (E)-methyl cinnamyl carbonate 
• 269409-70-3 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol 
• 1616917-67-9 (E)-2-(4-(cinnamyloxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 4392-24-9 Cinnamyl bromide 

Downstream Products

• 34591-21-4 4-(3-phenylpropyl)phenol 

Relevant academic research and scientific papers

Allylic alcohols as substrate for ruthenium-catalyzed C-C coupling allylation reactions: Preliminary communication

Allylic alcohols, rather than halides, acetates, or carbonates can be used directly in the Friedel-Crafts-type coupling with various phenols. The use of a RuIV, rather than a RuII, precursor promotes the formation of one H per cycle

[Pd]-Catalyzedpara-selective allylation of phenols: access to 4-[(E)-3-aryl/alkylprop-2-enyl]phenols

4-[(E)-3-Arylprop-2-enyl]phenols are omnipresent scaffolds and constitute natural products and biologically significant compounds. Obtusastyrene and obtustyrene are two such phenolic-based natural products isolated fromDalbergia retusa. The development of strategies based on a site-selective allylation, particularly protecting group-free substrates and non-activated coupling agents, is indispensable in organic synthesis. Herein, we present a highly regioselective [Pd]-catalyzedpara-allylation of phenols using simple, inactivated allylic alcohols as allylating coupling partners. Notably, this strategy is successful in open-air and under mild reaction conditions. Besides, the efficacy of the present protocol was demonstrated by the direct synthesis of obtusastyrene and obtustyrene.

Catalytic allylic arylation of cinnamyl carbonates over palladium nanoparticles supported on a thermoresponsive polymer in water

Poly(NIPAM-co-4-VP) undergoes a phase transition at the low critical solution temperature with a change from the hydrophilic to the hydrophobic core in a hydrophilic solvent. Palladium nanoparticles supported on such a thermoresponsive polymer support were demonstrated to catalyze the Tsuji-Trost reaction for the arylation of various cinnamyl carbonates by arylboronic acids. Therefore, a protocol developed using mild reaction conditions demonstrates the recyclability of the catalyst in an eco-friendly solvent such as water.

Hydrazone-palladium-catalyzed allylic arylation of cinnamyloxyphenylboronic acid pinacol esters

Allylic arylation of cinnamyloxyphenylboronic acid pinacol esters 3, which have arylboronic acid moiety and allylic ether moiety, using a hydrazone 1d-Pd(OAc)2 system proceeded and gave the corresponding 1,3-diarylpropene derivatives 4 with a phenolic hydroxyl group via a selective coupling reaction of the π-allyl intermediate to the boron-substituted position of the leaving group.

Bronsted acid-catalyzed nucleophilic substitution of alcohols

Simple Bronsted acids such as p-toluene-sulfonic acid monohydrate (PTS) or polymer-bound p-toluenesulfonic acid efficiently catalyze the direct nucleophilic substitution of the hydroxy group of allylic and benzylic alcohols with a large variety of carbon- and heteroatom-centered nucleophiles. Reaction conditions are mild, the process is conducted under an atmosphere of air without the need for dried solvents, and water is the only side product of the reaction.

High-yield ruthenium-catalyzed Friedel-Crafts-type allylation reactions using dicationic RuIV catalysts

(Chemical Equation Presented) Unexpected linkage: The use of dicationic RuIV complexes in the Friedel-Crafts-type allylation of aromatic alcohols leads unexpectedly to the formation of a new C-C bond and not to the phenolation product (see sche

A convenient and improved montmorillonite K-10 catalysed Friedel-Crafts benzylation and allylation with activated esters

Benzyl benzoate and cinnamyl acetate has been effectively used respectively as alkylating and allylating substrates in Friedel-Crafts reaction catalysed by montmorillonite K-10 clay.

Methods in synthesis of flavonoids. Part 3: Molybdenum(IV)-catalyzed coupling of cinnamyl alcohols to phenol derivatives

This paper deals with the formal total synthesis of flavonoids bearing the hydroxylation pattern of the catechin series based on an access to the fully functionalized skeleton via the alkylation of phloroglucinol tribenzyl ether by 3,4-dibenzyloxycinnamyl alcohol. This reaction was revealed to be most successful when catalyzed by the Mo(acac)2(SbF6)2 complex. In addition, the underlying concepts to the different ways that can be used in this C6-C3+C6 strategy are discussed.

Molybdenum(II)-catalyzed allylation of electron-rich aromatics and heteroaromatics

The stable, readily available molybdenum(II) complexes [Mo(CO)4Br2]2 (B) and Mo(CO)3(MeCN)2-(SnCl3)Cl (C) have been found to catalyze C-C bond- forming allylic substitution with electronrich aromatics (e.g., 15 + PhOMe → 62) and heteroaromatics (e.g., 15 + 36 → 88) as nucleophiles under mild conditions (room temperature, 30 min-3 h). Remarkable is the para-selectivity for anisole, whereas phenol tends to favor ortho-substitution in certain instances. Mechanistic and stereochemical experiments are indicative of Lewis-acid catalysis rather than a metal template-controlled process.