186465-05-4

Upstream product

• 3401-47-6 1-bromo-2-methoxynaphthalene 
• 4688-76-0 2-Biphenylboronic acid 
• 573-97-7 1-bromo-2-naphthol 

Downstream Products

• 218961-93-4 4-Biphenyl-2-yl-3-methoxymethoxy-naphthalene-2-carbaldehyde 
• 218961-92-3 1-Biphenyl-2-yl-2-methoxymethoxy-naphthalene 
• 186492-29-5 1-(2-phenylphenyl)-2-naphthol 
• 218961-91-2 Carbonic acid 1-biphenyl-2-yl-naphthalen-2-yl ester (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 

Relevant academic research and scientific papers

Catalytic and highly enantioselective aziridination of styrene derivatives

Highly enantioselective catalytic aziridination of styrene derivatives was realized by using the newly designed (salen)manganese(III) complex as a catalyst.

Synthesis of a class of binaphthyl monophosphine ligands with a naphthofuran skeleton and their applications in Suzuki-Miyaura coupling reactions

A series of new monophosphine ligands containing a naphthofuran skeleton have been prepared, characterized and evaluated in palladium-catalyzed Suzuki-Miyaura coupling reactions. Using Pd2(dba)3-L6 as the catalyst the reactions were performed with high catalytic activity under mild reaction conditions and the desired coupling products were obtained in good to excellent yields. The new catalyst system also showed broad substrate adaptability and practicality for gram-scale production.

Phosphine ligand containing benzofuran structure and preparation method and application thereof

The invention discloses phosphine ligand containing a benzofuran structure and a preparation method and application thereof. The phosphine ligand is a compound with a chemical structural formula shown in a formula (I) or an enantiomer or racemate of the compound. According to the phosphine ligand disclosed by the invention, a furan nucleus is introduced, so that electron cloud density of the aromatic nucleus of the phosphine ligand is improved, and steric hindrance is changed; thus, the phosphine ligand has the characteristics of good reaction activity and high yield of 99% when being applied to palladium-catalysis Suzuki-Miyaura model reaction. The phosphine ligand containing the benzofuran structure disclosed by the invention has a simple synthesizing method, is low in cost and is suitable for palladium-catalysis Suzuki-Miyaura reaction of varieties of substances.

(Planar-Chiral) Ferrocenylmethanols: From Anionic Homo Phospho-Fries Rearrangements to α-Ferrocenyl Carbenium Ions

The reaction of FcCH2OH with chlorophosphates gave ferrocenyl phosphates FcCH2OP(O)(OR)2 [Fc = Fe(η5-C5H5)(η4-C5H4)], which readily separate into phosphate anions and ferrocenyl carbo-cations. The latter species undergoes consecutive reactions, for example, electrophilic aromatic substitutions. When nitriles, instead of alcohols, are treated with FcLi or tBuLi and chlorophosphates, chiral-pool based ferrocenylimino phosphoramidates Fc-CR=N-P(O)(OR*)2 are formed, which are promising candidates for anionic homo phospho-Fries rearrangements. Moreover, the sterically demanding chiral chlorophosphate with R* enabled oxidative couplings of the imines to form a diferrocenylazine. Similarly, the reaction of Fc–Li with 9-anthrylnitrile produced a 10-ferrocenyl-substituted product, contrary to a reaction at the C≡N functionality. A planar-chiral ortho-P(S)Ph2-functionalized ferrocenylmethanol also gave carbo-cations under acidic conditions. These species can be sulfurized in a unique way giving thio ethers, whereby the in situ formed 1,2-P(S)Ph2,CH2+ ferrocene cation acts as the sulfur and electron source. However, lowering the substrate concentration prevents sulfur migration, resulting in electrophilic substitution reactions with aromatic solvents. Planar-chiral ferrocenylmethyl thio or anisyl derivatives were applied as ligands in Pd-catalyzed Suzuki–Miyaura C,C cross-couplings for the atroposelective synthesis of hindered biaryls with up to 26 % ee at low catalyst loadings (1 mol-% Pd).

Anionic phospho-fries rearrangement at ferrocene: One-pot approach to P,O-substituted ferrocenes

For the first time the anionic phospho-Fries rearrangement has been successfully applied in ferrocene chemistry, giving access to 1,2-P,O-substituted ferrocenes. The 1,3 (O → C)-migration occurs at ferrocenyl phosphates, thiophosphates, phosphite-borane adducts, and phosphinates by treatment with a base such as lithium diisopropylamide at low temperature, whereas the highest yields were obtained starting from diethylferrocenyl phosphate. Complete reduction of the phosphonate to a primary phosphine and subsequent Stelzer P,C cross coupling allowed the synthesis of Fe(η5-C5H3-2-OMe-PPh2) (η5-C5H5) (1). The qualification of 1 as a supporting ligand in palladium-catalyzed Suzuki-Miyaura C,C couplings has been proven by the synthesis of sterically congested tri-ortho-substituted biaryls under mild reaction conditions in good to excellent yields.

A Planar-Chiral Phosphino(alkenyl)ferrocene for Suzuki-Miyaura C-C Coupling Reactions

Planar-chiral phosphinoferrocene [Fe(η5-C5H3-1-PPh2-2-(E)-CH=CHPh)(η5-C5H5)] (4) was applied in the presence of palladium in Suzuki-Miyaura couplings for the synthesis of sterically congested biaryls. The catalytic activity arises from homogeneous palladium phosphine complexes, of which the potential pre-catalyst [Pd(4)2Cl2] was characterized structurally. The catalytic system is excellently suited for the synthesis of tri-ortho-substituted biaryls under mild conditions (0.1 mol-%, 50-100 C), whereas its application towards the synthesis of tetra-ortho-substituted biaryls is quite limited. Comparing the performance of the reaction with 4 as catalyst and a range of substrates with differing ortho substituents suggests that transmetalation is rate determining. Complex (Sp)-4 was used in atropselective couplings, wherein enantioenrichments of up to 36 % were achieved. The stereoselectivity depends to some extent on the steric properties of the boronic acids; however, slight changes at the aryl halides influence the enantioselectivity.

Robust acenaphthoimidazolylidene palladium complexes: Highly efficient catalysts for suzuki-miyaura couplings with sterically hindered substrates

Robust acenaphthoimidazolylidene palladium complexes have been demonstrated as highly efficient and general catalysts for the sterically hindered Suzuki-Miyaura cross-coupling reactions in excellent yields even with low catalyst loadings under mild reaction conditions. The high catalytic activity of these complexes highlights that, besides the "flexible steric bulky" concept, σ-donor properties of the NHC ligands are also crucial to accelerate the transformations.