140423-65-0

Upstream product

• 67-56-1 methanol 
• 109-72-8 n-butyllithium 
• 104-94-9 4-methoxy-aniline 
• 637-69-4 4-Methoxystyrene 
• 696-62-8 para-iodoanisole 
• 19234-04-9 2-(p-methoxyphenyl)-benzo[b]furan 
• 98437-24-2 benzofuran-2-boronic acid 
• 133642-09-8 C₁₉H₂₇N₂O₄P 
• 123-11-5 4-methoxy-benzaldehyde 
• 1833-44-9 1-bromo-2-((trimethylsilyl)methyl)benzene 
• 140423-60-5 2-[2-Hydroxy-2-(4-methoxy-phenyl)-ethyl]-phenol 
• 56184-99-7 o-Tolyl N,N,N',N'-tetramethylphosphorodiamidate 

Relevant academic research and scientific papers

Efficient one-pot synthesis of 2-aryldihydrobenzofuran

A series of 2-aryldihydrobenzofuran derivatives were successfully synthesized from the corresponding carbonyl compounds and (2-bromobenzyl) trimethylsilane by the one-pot benzylation-substitution procedure. Georg Thieme Verlag Stuttgart.

Enantioselective Oxy-Heck–Matsuda Arylations: Expeditious Synthesis of Dihydrobenzofuran Systems and Total Synthesis of the Neolignan (?)-Conocarpan

This work discloses the first examples of an effective enantioselective oxy-Heck–Matsuda reaction using a variety of styrenic olefins to generate chiral dihydrobenzofurans. The reaction proceeds in moderate to good yields, with high trans diastereoselectivity (up to 20:1) in enantioselectivities up to 90:10 using the N,N-ligand pyrimidine-bisoxazoline (PyriBox). The oxy-Heck–Matsuda reactions were carried out under mild conditions and rather low catalyst loadings. The feasibility and practicality of the process is demonstrated by a concise total synthesis of the neolignan (?)-conocarpan. X-ray diffraction of an advanced brominated intermediate in the route to (?)-conocarpan has allowed the unequivocal assignment of the absolute stereochemistry of the oxy-Heck–Matsuda aryldihydrobenzofuran products. A rationale for the mechanism operating in these enantioselective oxy-Heck–Matsuda reactions is also presented. (Figure presented.).

One-pot synthesis of substituted indoles via titanium(iv) alkoxide mediated imine formation-copper-catalyzed N-arylation

Readily accessible o-bromobenzylketones and primary alkyl amines and anilines were used for the construction of substituted indoles in good to excellent yields. The sequence involves a titanium-mediated reaction of ketones with amines to afford imines and subsequent intramolecular cyclization into indoles employing copper catalysis. The two-step protocol allows for the preparation of indoles bearing both N-alkyl and N-aryl groups as well as N-unsubstituted indoles without isolation of the intermediates and is tolerant of a wide range of functionality.

Ruthenium NHC catalyzed highly asymmetric hydrogenation of benzofurans

H2-O-T! Aromatic O-heterocycles are a challenging substrates for asymmetric hydrogenation (H2). An in situ formed chiral N-heterocyclic carbene (NHC) ruthenium complex allows the high yielding, completely regioselective, and highly asymmetric hydrogenation of substituted benzofurans at room Temperature, giving valuable 2,3-dihydrobenzofurans (see scheme). Copyright

Ambident effect of a p-sulfinyl group for the introduction of two carbon substituents to phenol rings: a convergent synthesis of diverse benzofuran neolignans.

A convergent synthesis of diversely substituted benzofuran neolignans (8) is described employing a single p-sulfinyl group on the phenols (3) as an ambident functional group for two types of carbon-carbon bond-forming reactions: (i) the direct synthesis of the dihydrobenzofuran skeletons through an aromatic Pummerer-type reaction and (ii) the ipso-substitution of the sulfur functional group by carbon substituents through a ligand exchange reaction.

A regioselective lithiation of ortho-cresols using the bis(dimethylamino)phosphoryl group as a directing group: General synthesis of 2,3-dihydrobenzo[b]furans including naturally occurring neolignans

A general synthetic method was developed for 2-aryl-2,3-dihydrobenzo[b]furans via regioselective lithiation of ortho-tolyl tetramethylphosphorodiamidates followed by addition of aromatic aldehydes as a key step. ortho-Tolyl tetramethylphosphorodiamidates