564483-19-8 Usage
Description
2-Di-tert-butylphosphino-2',4',6'-triisopropylbiphenyl, also known as tBuXPhos, is an air-stable, electron-rich biaryl phosphine ligand developed by the Buchwald group to enhance the reactivity of palladium catalysis during cross-coupling reactions.
Uses
Used in Cross-Coupling Reactions:
tBuXPhos is used as a ligand for palladium-catalyzed cross-coupling reactions to improve the reactivity and efficiency of these processes. It is particularly effective in reactions such as:
Palladium-catalyzed Tsuji-Trost substitution and cross-coupling of benzylic fluorides.
Palladium-catalyzed C-N cross-coupling of sulfinamides and aryl halides.
Palladium-catalyzed rapid methoxylation and deuteriomethoxylation of bromo-chalcones.
Used in Suzuki Reaction:
tBuXPhos is an effective ligand for the Pd-catalyzed arylation of pyrazoles, indazoles, and amino heterocycles, which are important in the Suzuki reaction, a widely used cross-coupling reaction in organic chemistry.
Used in Gold Catalysis:
tBuXPhos has been used in the preparation of [tBuXPhosAu(MeCN)]BAr4F, a gold catalyst for the intermolecular [2+2] cycloaddition of terminal arylalkynes with substituted alkenes to form functionalized cyclobutenes with high regioselectivity.
Used in C-O and C-N Bond Formation:
tBuXPhos is a ligand for Pd-catalyzed C-O and C-N bond formation, which are crucial in the synthesis of various organic compounds and pharmaceuticals.
Reactions
Effective ligand for the Pd-catalyzed arylation of pyrazoles, indazoles and amino heterocycles.
Ligand used in the Pd-catalyzed synthesis of phenols from aryl halides and KOH.
Ligand used in the Pd-catalyzed of benzoic acids from aryl halides and CO2.
Ligand used in the Pd-catalyzed trifluoromethylation of vinyl sulfonates.
Ligand used in the Pd-catalyzed arylation of nitroacetates.
Ligand used in the Pd-catalyzed Suzuki?Miyaura cross-coupling of allylboronates and aryl halides.
Ligand used in the Pd-catalyzed cyanation of (hetero)arylchlorides and bromides.
Ligand used in the Pd-catalyzed C–N cross coupling of sulfinamides and aryl halides.
Ligand used in the Pd-catalyzed arylation of cyanamides.
Check Digit Verification of cas no
The CAS Registry Mumber 564483-19-8 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 5,6,4,4,8 and 3 respectively; the second part has 2 digits, 1 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 564483-19:
(8*5)+(7*6)+(6*4)+(5*4)+(4*8)+(3*3)+(2*1)+(1*9)=178
178 % 10 = 8
So 564483-19-8 is a valid CAS Registry Number.
564483-19-8Relevant articles and documents
Synthesis of di-tert-butylphenol [...] biphenyl compounds (by machine translation)
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Paragraph 0013, (2019/03/06)
The invention discloses a method for synthesizing tert-[...] biphenyl compounds, which belongs to the field of organic synthesis. In the oxygen free atmosphere, in order to di-tert-butylphenol [...] as raw material, under the action of the palladium catalyst, with the O-bromophenylacetic reaction, then the obtained by coupling with aryl boric acid di-tert-butylphenol [...] biphenyl compound. Compared with the prior art the invention less reaction steps, the operation is simple, high yield, is more suitable for industrial production. (by machine translation)
Expanding Pd-catalyzed C-N bond-forming processes: The first amidation of aryl sulfonates, aqueous amination, and complementarity with Cu-catalyzed reactions
Huang, Xiaohua,Anderson, Kevin W.,Zim, Danilo,Jiang, Lei,Klapars, Artis,Buchwald, Stephen L.
, p. 6653 - 6655 (2007/10/03)
The first general method for the Pd-catalyzed amination of aryl tosylates and benzenesulfonates was developed utilizing ligand 1, which belongs to a new generation of biaryl monophosphine ligands. In addition, the new catalyst system for the first time enables amidation of aryl arenesulfonates and aqueous amination protocols that do not necessitate the use of cosolvents. The substrate scope has been significantly expanded to include aryl halides containing primary amides and free carboxylic acid groups. In the case of multifunctional substrates, the Pd-catalyzed amination can provide selectivity that is complementary to the Cu-catalyzed C-N bond-forming processes. Copyright