247940-06-3 Usage
Description
2-(Dicyclohexylphosphino)biphenyl, also known as CyJohnPhos, is an air-stable, bulky, and electron-rich monodentate biarylphosphine ligand developed by the Buchwald group. It is characterized by its white to light yellow crystal powder appearance and is designed to enhance the reactivity of palladium catalysis during cross-coupling reactions.
Uses
Used in Pharmaceutical Industry:
2-(Dicyclohexylphosphino)biphenyl is used as a ligand for the Pd-catalyzed synthesis of aromatic amines using aryl chlorides, bromides, and triflates. This application is particularly relevant in the pharmaceutical industry, where the synthesis of aromatic amines is crucial for the production of various drugs and medicinal compounds.
Used in Chemical Synthesis:
In the field of chemical synthesis, 2-(Dicyclohexylphosphino)biphenyl is used as a catalyst for Suzuki coupling reactions. This reaction is a widely employed method for the formation of carbon-carbon bonds, which are essential in the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and advanced materials.
Used in Cross-Coupling Reactions:
2-(Dicyclohexylphosphino)biphenyl is also used in cross-coupling reactions, which are fundamental in organic chemistry and materials science. These reactions involve the formation of new carbon-carbon or carbon-heteroatom bonds and are essential for the synthesis of complex molecular structures and the development of new materials with specific properties.
Reaction
Ligand used in the palladium-catalyzed synthesis of aromatic amines from aryl chlorides, bromides and triflates.
Ligand employed in Suzuki coupling reactions involving aryl chlorides, bromides and triflates.
Useful ligand for the Pd-catalyzed oxidation of alcohols in the presence of chlorobenzenes.
Useful ligand for the Pd-catalyzed amination with ammonia equivalents.
Ligand for the gold(I)-catalyzed intramolecular [4+2] cycloadditions involving 1,3-enynes and arylalkynes with alkenes.
Ligand used in the palladium-catalyzed borylation of aryl bromdies.
Ligand used in the palladium-catalyzed siliylation of aryl chlorides.
Check Digit Verification of cas no
The CAS Registry Mumber 247940-06-3 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 2,4,7,9,4 and 0 respectively; the second part has 2 digits, 0 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 247940-06:
(8*2)+(7*4)+(6*7)+(5*9)+(4*4)+(3*0)+(2*0)+(1*6)=153
153 % 10 = 3
So 247940-06-3 is a valid CAS Registry Number.
InChI:InChI=1/C24H31P/c1-4-12-20(13-5-1)23-18-10-11-19-24(23)25(21-14-6-2-7-15-21)22-16-8-3-9-17-22/h1,4-5,10-13,18-19,21-22H,2-3,6-9,14-17H2
247940-06-3Relevant articles and documents
A Mild One-Pot Reduction of Phosphine(V) Oxides Affording Phosphines(III) and Their Metal Catalysts
Kapu?niak, ?ukasz,Plessow, Philipp N.,Trzybiński, Damian,Wo?niak, Krzysztof,Hofmann, Peter,Jolly, Phillip Iain
, p. 693 - 701 (2021/04/06)
The metal-free reduction of a range of phosphine(V) oxides employing oxalyl chloride as an activating agent and hexachlorodisilane as reducing reagent has been achieved under mild reaction conditions. The method was successfully applied to the reduction of industrial waste byproduct triphenylphosphine(V) oxide, closing the phosphorus cycle to cleanly regenerate triphenylphosphine(III). Mechanistic studies and quantum chemical calculations support the attack of the dissociated chloride anion of intermediated phosphonium salt at the silicon of the disilane as the rate-limiting step for deprotection. The exquisite purity of the resultant phosphine(III) ligands after the simple removal of volatiles under reduced pressure circumvents laborious purification prior to metalation and has permitted the facile formation of important transition metal catalysts.
Rhodium-Catalyzed PIII-Directed ortho-C?H Borylation of Arylphosphines
Wen, Jian,Wang, Dingyi,Qian, Jiasheng,Wang, Di,Zhu, Chendan,Zhao, Yue,Shi, Zhuangzhi
supporting information, p. 2078 - 2082 (2019/02/01)
Transition-metal-mediated metalation of an aromatic C?H bond that is adjacent to a tertiary phosphine group in arylphosphines via a four-membered chelate ring was first discovered in 1968. Herein, we overcome a long-standing problem with the ortho-C?H activation of arylphosphines in a catalytic fashion. In particular, we developed a rhodium-catalyzed ortho-selective C?H borylation of various commercially available arylphosphines with B2pin2 through PIII-chelation-assisted C?H activation. This discovery is suggestive of a generic platform that could enable the late-stage modification of readily accessible arylphosphines.
Preparation of Aryl(dicyclohexyl)phosphines by C-P Bond-Forming Cross-Coupling in Water Catalyzed by an Amphiphilic-Resin-Supported Palladium Complex
Hirai, Yoshinori,Uozumi, Yasuhiro
supporting information, p. 2966 - 2970 (2017/10/26)
Aryl(dicyclohexyl)phosphines were prepared by a catalytic C-P bond-forming cross-coupling reaction of haloarenes with dicyclohexylphosphine under heterogeneous conditions in water containing an immobilized palladium complex coordinated to an amphiphilic polystyrene-poly(ethylene glycol) resin supported di(tert -butyl)phosphine ligand.