产品名称
2-二环己基膦基-2′,6′-二甲氧基联苯基, 95%
assay
95%
form
powder or crystals
reaction suitability
reaction type: Buchwald-Hartwig Cross Coupling Reaction, reaction type: Heck Reaction, reaction type: Hiyama Coupling, reaction type: Negishi Coupling, reaction type: Sonogashira Coupling, reaction type: Stille Coupling, reaction type: Suzuki-Miyaura Coupling, reagent type: catalyst
reaction type: Cross Couplings, reagent type: ligand
greener alternative product characteristics
Catalysis
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sustainability
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mp
164-166 °C (lit.), 165.5 °C
functional group
phosphine
greener alternative category
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General description
SPhos [2-Dicyclohexylphosphino-2′, 6′-dimethoxybiphenyl] 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.
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Application
用于Suzuki-Miyaura偶联反应的高度通用配体； 芳基氯、受阻联芳基、杂联芳基。
SPhos may be used as a ligand in the following processes:
- Palladium catalyzed Suzuki-Miyaura cross-coupling reaction between Boc-protected aminomethyltrifluoroborate and aryl chlorides or hetaryl chlorides to form the corresponding aminomethylarenes.
- Palladium catalyzed Suzuki-Miyaura cross-coupling reaction between 4-methyl-substituted piperidinylzinc reagent and different aryl or heteroaryl iodides to form various substituted piperidines.
- Intramolecular Suzuki-Miyaura coupling to form the 18-membered macrocyclic ring during the multi-step synthesis of riccardin C.
Utilized in conjunction with palladium to form a highly active catalyst for C-N bond formation
Legal Information
使用涉及的专利号：US 6307087；EP 1097158；JP 5758844；CA 2336691
存储类别
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Highly diastereoselective arylations of substituted piperidines
Seel, Stephanie, et al.
Journal of the American Chemical Society, 133.13, 4774-4777 (2011)
What makes for a good catalytic cycle? A theoretical study of the SPhos ligand in the Suzuki?Miyaura reaction
Kozuch, Sebastian, and Jan ML Martin
Chemical Communications (Cambridge, England), 47.17, 4935-4937 (2011)
Use of the SPhos Ligand to Suppress Racemization in Arylpinacolboronate Ester Suzuki Couplings Involving ?-Amino Acids. Synthesis of Biaryl Derivatives of 4-Hydroxyphenylglycine, Tyrosine, and Tryptophan
Prieto, Monica, et al.
The Journal of Organic Chemistry, 74.23, 9202-9205 (2009)
Evidence for the formation and structure of palladacycles during Pd-catalyzed C-N bond formation with catalysts derived from bulky monophosphinobiaryl ligands.
Eric R Strieter et al.
Angewandte Chemie (International ed. in English), 45(6), 925-928 (2005-12-29)
Synthesis of riccardin C and its seven analogues. Part 1: The role of their phenolic hydroxy groups as LXR? agonists
Hioki, Hideaki, et al.
Bioorganic & Medicinal Chemistry Letters, 19.3, 738-741 (2009)
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