22082-95-7

Upstream product

• 93-04-9 2-Methoxynaphthalene 
• 346656-39-1 2-(2-fluorophenyl)-5,5-dimethyl-[1,3,2]dioxaborinane 
• 7385-85-5 naphthalen-2-yl tosylate 
• 16463-37-9 potassium ortho-fluorobenzoate 
• 1072-85-1 o-fluorobromobenzene 
• 580-13-2 2-bromonaphthalene 
• 1993-03-9 o-fluorophenylboronic acid 
• 135-19-3 β-naphthol 
• 3857-83-8 2-naphthyl triflate 
• 1145-08-0 naphthalen-2-yl N,N-dimethylsulfamic acid 

Relevant academic research and scientific papers

Nickel-catalyzed cross-coupling of aryl methyl ethers with aryl boronic esters

(Chemical Equation Presented) To C-OMe and go: The title reaction, involving cleavage of a C-OMe bond, is demonstrated for the coupling of aryl methyl ethers on fused aromatic systems, such as naphthalene and phenanthrene, as well as anisoles containing electron-withdrawing groups with a wide range of boronic esters. cod=cycloocta-1,5-diene, Cy=cyclohexyl.

Cross-Electrophile C(sp2)?Si Coupling of Vinyl Chlorosilanes

The cross-electrophile coupling has become a powerful tool for C?C bond formation, but its potential for forging the C?Si bond remains unexplored. Here we report a cross-electrophile Csp2-Si coupling reaction of vinyl/aryl electrophiles with vinyl chlorosilanes. This new protocol offers an approach for facile and precise synthesis of organosilanes with high molecular diversity and complexity from readily available materials. The reaction proceeds under mild and non-basic conditions, demonstrating a high step economy, broad substrate scope, wide functionality tolerance, and easy scalability. The synthetic utility of the method is shown by its efficient accessing of silicon bioisosteres, the design of new BCB-monomers, and studies on the Hiyama cross-coupling of vinylsilane products.

Tetraethylphosphorodiamidate-Directed Metalation Group: Directed Ortho and Remote Metalation, Cross Coupling, and Remote Phospha Anionic Fries Rearrangement Reactions

The linked directed ortho and remote metalation (DoM and DreM) and cross-coupling reactions of aryl phosphorodiamidates (Ar-OP(O)(NEt2)2) is reported. The o-iodo and o-boronato aryl tetraethylphosphorodiamidates 3, prepared by DoM, undergo orthogonal Ni- and Pd-catalyzed Suzuki-Miyaura cross coupling to furnish biaryls 4 and 5 in good to excellent yields. Silicon group protection of biaryl 4 via DoM followed by previously unobserved DreM phospha anionic Fries rearrangement affords biaryls 11 which, under acidic conditions, furnish oxaphosphorine oxides 12.

TBuLi-Mediated One-Pot Direct Highly Selective Cross-Coupling of Two Distinct Aryl Bromides

A Pd-catalyzed direct cross-coupling of two distinct aryl bromides mediated by tBuLi is described. The use of [Pd-PEPPSI-IPr] or [Pd-PEPPSI-IPent] as catalyst allows for the efficient one-pot synthesis of unsymmetrical biaryls at room temperature. The key for this selective cross-coupling is the use of an ortho-substituted bromide that undergoes lithium-halogen exchange preferentially. Bro to Bro: A palladium-catalyzed direct cross-coupling of two distinct aryl bromides mediated by tBuLi is described. The use of [Pd-PEPPSI-IPr] or [Pd-PEPPSI-IPent] as catalyst allows for the efficient one-pot synthesis of unsymmetrical biaryls at room temperature. The key for this selective cross-coupling is the use of an ortho-substituted bromide that undergoes lithium-halogen exchange preferentially.

Rapid nickel-catalyzed suzuki-miyaura cross-couplings of aryl carbamates and sulfamates utilizing microwave heating

High-speed and scalable nickel-catalyzed cross-coupling of arylboronic acids with aryl carbamates and sulfamates is achieved by using sealed-vessel microwave processing.(Figure Presented)

Decarboxylative cross-coupling of aryl tosylates with aromatic carboxylate salts

(Figure Presented) A bimetallic copper/palladium catalyst system is disclosed that enables the use of tosylates as carbon electrophiles in decarboxylative coupling reactions. A variety of aromatic carboxylate salts, regardless of their substitution pattern, have been coupled with these inexpensive and readily available electrophiles to give the corresponding biaryl compounds in good yields (see scheme).