22187-05-9

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• 91-20-3 naphthalene 
• 108-67-8 1,3,5-trimethyl-benzene 
• 90-11-9 1-Bromonaphthalene 
• 2633-66-1 2-mesitylmagnesium bromide 
• 576-83-0 2,4,6-trimethylphenyl bromide 
• 13922-41-3 1-Naphthylboronic acid 
• 68971-91-5 tri-n-butyl(mesityl)stannane 
• 90-13-1 1-Chloronaphthalene 
• 5980-97-2 mesitylboronic acid 
• 2216-69-5 1-Methoxynaphthalene 
• 125261-32-7 2,4,6-trimethylphenyl trifluoromethanesulfonate 
• 5806-59-7 mesityllithium 
• 130-14-3 sodium 1-naphthalenesulfonate 

Downstream Products

• 1260404-93-0 4,4'-dimesityl-1,1'-binaphthyl 

Relevant academic research and scientific papers

Air stable NHCs: A study of stereoelectronics and metallorganic catalytic activity

The air stable NHC IPrBr is reported. A stereoelectronic study of IPrBr and its similarly stable relative IMesBr demonstrates metal complex specific changes in NHC donicity versus the ubiquitous IPr and IMes. Application to a Suzuki coupling and an iridium transfer hydrogenation gives superior outcomes using IPrBr and IMesBr. This journal is

Stereoelectronic Characterization and Catalytic Potential of a 1,3-Bis(2,6-terphenyl)-Substituted N-Heterocyclic Carbene

The preparation of a 1,3-bis(2,6-terphenyl)imidazol-2-ylidene, IDitop (Ditop=2,6-bis(4-tolyl)phenyl-) is reported. Several late transition metal complexes as well as the selenium adduct of IDitop were prepared to study and compare the stereoelectronic properties of IDitop to other well-known N-heterocyclic carbenes (NHCs). A study of the steric character of IDitop taken from crystal structure data of the complexes and adducts reveals a high degree of flexibility. Preliminary application to challenging Suzuki coupling reactions was undertaken.

Allyl complexes for use in coupling reactions

A complex of formula (1), wherein, M is palladium or nickel, R1 and R2 are independently organic groups having 1-20 carbon atoms, or R1 and R2 are linked to form a ring structure with the phosphorus atom, R3 is selected from the group consisting of substituted and unsubstituted aryl, substituted and unsubstituted heteroaryl, and substituted and unsubstituted metallocenyl, R4 is an organic group having 1-20 carbon atoms, n is 0, 1, 2, 3, 4 or 5, X is an anionic ligand. A process for the preparation of the complex, and its use in carbon-carbon or carbon-nitrogen coupling reactions is also provided.

A Monophosphine Ligand Derived from Anthracene Photodimer: Synthetic Applications for Palladium-Catalyzed Coupling Reactions

Herein, we present an air-stable dianthracenyl monophosphine ligand (diAnthPhos) which can be prepared in two steps from commercially available anthracene derivatives. The ligand exhibits excellent efficiency for palladium-catalyzed coupling reactions. In particular, Miyaura borylation of heterocycle-containing electrophiles can be facilitated employing the diAnthPhos ligand with a broad substrate scope and low catalyst loading. The valuable synthetic utility of the new ligand is further demonstrated by a one-pot Miyaura borylation/Suzuki coupling protocol for heteroaryl-containing substrates.

Murahashi Cross-Coupling at ?78 °C: A One-Pot Procedure for Sequential C?C/C?C, C?C/C?N, and C?C/C?S Cross-Coupling of Bromo-Chloro-Arenes

The coupling of organolithium reagents, including strongly hindered examples, at cryogenic temperatures (as low as ?78 °C) has been achieved with high-reactivity Pd-NHC catalysts. A temperature-dependent chemoselectivity trigger has been developed for the selective coupling of aryl bromides in the presence of chlorides. Building on this, a one-pot, sequential coupling strategy is presented for the rapid construction of advanced building blocks. Importantly, one-shot addition of alkyllithium compounds to Pd cross-coupling reactions has been achieved, eliminating the need for slow addition by syringe pump.

(2 - Disubstituted [...]) -1 - alkyl - yinyin duo phosphine ligand and its synthesis method and application

The invention discloses (2-disubstituted phosphino-phenyl)-1-alkyl-indol-phosphine ligand and a synthetic method and application thereof. The structural formula of the (2-disubstituted phosphino-phenyl)-1-alkyl-indol-phosphine ligand is (please see the formula in the specification), wherein R is ethyl, or n-propyl, or isopropyl, or n-butyl, or isobutyl, or sec-butyl, or C5-C10 alkyl, or methyl cyanide, or methyl methoxyl, R' is phenyl, or ethyl, or isopropyl, or cyclohexyl, and R'' and R''' are methyl, or C5-C10 alkyl, or methyl methoxyl. The indole skeleton phosphine ligand is stable in air and easy to store and treat. Substituent groups on nitrogen in an indole skeleton are capable of adjusting electronic and spatial configuration of the whole ligand. It is critical that the ligand is easy to synthesize, high in total yield and easy to prepare through synthesis in quantity.

Readily available catalysts for demanding Suzuki–Miyaura couplings under mild conditions

A straightforward synthesis of a sterically hindered and electron rich bidentate monophosphine biaryl ligand Sym-Phos of C,P-type of complexation was realised in a high yield starting from simple substrates in easily affordable conditions. In combination with a palladium source, the obtained ligand formed a highly active catalyst mediating sterically demanding Suzuki–Miyaura coupling reactions in aqueous media even at 60 °C and with no need to protect the reaction mixture by an inert gas.

An efficient indenyl-derived phosphine ligand for the Suzuki-Miyaura coupling of sterically hindered aryl halides

An air-stable aryl substituted indenyl phosphine used in combination with Pd(OAc)2 provides a highly efficient catalyst for the Suzuki-Miyaura cross-coupling reaction of sterically hindered aryl halides with aryl boronic acids.

Nickel- or Cobalt-Catalyzed Cross-Coupling of Arylsulfonic Acid Salts with Grignard Reagents

The use of arylsulfonic acid salts as electrophiles in a nickel- or cobalt-catalyzed cross-coupling with Grignard reagents is described. Bis(tricyclohexylphosphine)nickel dichloride [NiCl2(PCy3)2] was found to be the optimal catalyst, and reactions with this catalyst proceeded in most cases at room temperature. The analogous cobalt catalyst [CoCl2(PCy3)2] was also found to promote the cross-coupling reaction at higher temperature (60C).

An Alternative Approach to PEPPSI Catalysts: From Palladium Isonitriles to Highly Active Unsymmetrically Substituted PEPPSI Catalysts

A series of new pyridine-enhanced precatalyst preparation, stabilization, and initiation (PEPPSI)-type complexes bearing different types of carbene ligands was prepared by the modular and convergent template synthesis strategy. Nitrogen acyclic carbenes, saturated and unsaturated five-membered NHC, saturated six-membered NHCs, and five-membered N-heterocyclic oxo-carbene (NHOC) ligands on palladium were prepared this way. These new organometallic compounds then were tested in Suzuki and Negishi cross-coupling reactions by using substrates with one or two substituents in ortho-position of the new C- C bond being formed. Both aryl chlorides and bromides were tested as coupling partners. In some cases, the new ligands gave results similar to Organ's successful IPr-based and IPent-based PEPPSI derivatives, with aryl bromides 0.05 mol % catalyst load still gave satisfactory results, with aryl chlorides 0.5 mol % were needed.