186891-19-0

Upstream product

• 1592-38-7 2-Naphthalenemethanol 
• 66-99-9 β-naphthaldehyde 
• 939-26-4 2-bromomethylnaphthyl bromide 
• 619-42-1 4-methoxycarbonylphenyl bromide 
• 1632070-89-3 potassium trifluoro(naphthalen-2-ylmethyl)borate 
• 19350-74-4 2-naphthaldehyde tosylhydrazone 
• 107647-65-4 tributyl(naphthalen-2-ylmethyl)stannane 
• 905966-40-7 methyl 4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzoate 
• 42101-92-8 2-naphthylmethyl methyl ether 
• 21473-01-8 2-naphthalenylmagnesium bromide 
• 186891-04-3 methyl 4-(hydroxy(naphthalen-2-yl)methyl)benzoate 
• 1571-08-0 methyl 4-formylbenzoate 

Downstream Products

• 174568-24-2 2-(4-Naphthalen-2-ylmethyl-benzoylamino)-benzoic acid methyl ester 
• 70121-90-3 4-(2-naphthylmethyl)benzoic acid 

Relevant academic research and scientific papers

Nickel-Catalyzed Reductive Cross-Coupling of Benzylic Sulfonium Salts with Aryl Iodides

A nickel-catalyzed cross-electrophile coupling of benzylic sulfonium salts with aryl iodides has been developed, providing direct access to diarylalkanes from readily available and stable coupling partners. Preliminary mechanistic studies suggest that the C-S bond cleavage proceeds through a single-electron transfer process to generate a benzylic radical.

Nickel-Catalyzed Electrochemical C(sp3)?C(sp2) Cross-Coupling Reactions of Benzyl Trifluoroborate and Organic Halides**

Reported here is the redox neutral electrochemical C(sp2)?C(sp3) cross-coupling reaction of bench-stable aryl halides or β-bromostyrene (electrophiles) and benzylic trifluoroborates (nucleophiles) using nonprecious, bench-stable NiCl2?glyme/polypyridine catalysts in an undivided cell configuration under ambient conditions. The broad reaction scope and good yields of the Ni-catalyzed electrochemical coupling reactions were confirmed by 50 examples of aryl/β-styrenyl chloride/bromide and benzylic trifluoroborates. Potential applications were demonstrated by electrosynthesis and late-stage functionalization of pharmaceuticals and natural amino acid modification, and three reactions were run on gram-scale in a flow-cell electrolyzer. The electrochemical C?C cross-coupling reactions proceed through an unconventional radical transmetalation mechanism. This method is highly productive and expected to find wide-spread applications in organic synthesis.

Synthesis of Benzyltributylstannanes by the Reaction of N-Tosylhydrazones with Bu3SnH

An efficient stannylation process with N-tosylhydrazones or directly with carbonyl compounds has been developed. A series of functionalized benzyl- and alkyltributylstannanes can be synthesized in moderate to good yields under transition-metal-free conditions. Tandem transformations involving stannylation/Stille cross-coupling reaction have been carried out without purification of the benzyltributylstannane intermediates to afford a series of diarylmethane derivatives.

Alcohols as Latent Coupling Fragments for Metallaphotoredox Catalysis: Sp3-sp2 Cross-Coupling of Oxalates with Aryl Halides

Alkyl oxalates, prepared from their corresponding alcohols, are engaged for the first time as carbon radical fragments in metallaphotoredox catalysis. In this report, we demonstrate that alcohols, native organic functional groups, can be readily activated with simple oxalyl chloride to become radical precursors in a net redox-neutral Csp3-Csp2 cross-coupling with a broad range of aryl halides. This alcohol-activation coupling is successfully applied to the functionalization of a naturally occurring steroid and the expedient synthesis of a medicinally relevant drug lead.

Direct cross-coupling of benzyl alcohols to construct diarylmethanes via palladium catalysis

A direct arylation to furnish diarylmethanes from benzyl alcohols was realized through Pd(PPh3)4-catalyzed Suzuki-Miyaura coupling via benzylic C-O activation in the absence of any additives. The arylation is compatible with various functional groups. This development provides an atom- and step-economic way to approach a diarylmethane scaffold under mild and environmentally benign conditions. This journal is

1,3-dicyclohexylimidazol-2-ylidene as a superior ligand for the nickel-catalyzed cross-couplings of aryl and benzyl methyl ethers with organoboron reagents

A new catalytic system has been developed involving the use of Ni(cod)2 in conjunction with 1,3-dicyclohexylimidazol-2-ylidene for the cross-coupling of aryl and benzyl methyl ethers with organoboron reagents. This method not only allows for the use of readily available methyl ethers as halide surrogates but also provides a functional group tolerant method for the late-stage derivatization of complex molecules.

Novel naphthalene derivatives as inhibitors of human immunoglobulin E antibody production

A series of naphthalene derivatives with a variety of substituents at the 2-position was prepared in order to evaluate their suppressive effect on immunoglobulin E (IgE) antibody production by human peripheral blood mononuclear cells provoked with anti-CD40 antibody (α-CD40), interleukin-4 (IL-4), and interleukin-10 (IL-10). Compounds having a 1,4-phenylene spacer moiety tethered between the 2-naphthyl nucleus and anthranilic acid suppressed IgE antibody production in vitro in preference to that of IgG antibody without affecting cell viability. Deletion of the anthranilic acid moiety diminished the inhibitory activities. Changing the 2-naphthyl to a 1- naphthyl or phenyl nucleus led to no change in the potency, indicating that the aromatic group at this position is indispensable for the inhibitory activities. On the other hand, changing the 1,4-phenylene spacer to a 1,3- phenylene one resulted in reduced potency. Similarly, inhibitory activities were lost when the CO2H moiety at the 2-position was moved to the 3- or 4- position on the terminal benzene. These observations suggest that the conformation around the anthranilic acid moiety affects the inhibitory activities toward IgE biosynthesis, 2-(4-(2-Naphthyloxy)benzamido)benzoic acid (29) seemed to be a more potent inhibitor of IgE production than of IgG production. Insertion of a methylene between the inter-phenylene and the amide moiety resulted in 2-((4-(2-naphthyloxy)phenyl)acetamido)benzoic acid (31), which provided a stronger inhibition of both IgE and IgG production, although the selectivity toward IgE was lower than that of 29. Introduction of a benzyl group at the 6-position on the naphthalene ring considerably increased the inhibitory activity toward IgE production with an IC50 of 8.3 nM (36). The potency of 31 and 36 was retained when hydrocortisone or lipopolysaccharide was used instead of α-CD40 and IL-10 as costimulatory factors with IL-4, implying that these compounds may interfere with signal transduction between IL-4/IL-4 receptor cognition and genetic transcription that induce class-switching of immunoglobulin in B cells. These novel naphthalene derivatives are thus excellent candidates for further investigation with a view toward a therapeutic remedy against IgE-mediated allergic diseases.