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检测方案
95%
形式
powder or crystals
反应适用性
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
mp
164-166 °C (lit.)
165.5 °C
官能团
phosphine
SMILES字符串
COc1cccc(OC)c1-c2ccccc2P(C3CCCCC3)C4CCCCC4
InChI
1S/C26H35O2P/c1-27-23-17-11-18-24(28-2)26(23)22-16-9-10-19-25(22)29(20-12-5-3-6-13-20)21-14-7-4-8-15-21/h9-11,16-21H,3-8,12-15H2,1-2H3
InChI key
VNFWTIYUKDMAOP-UHFFFAOYSA-N
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一般描述
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.
应用
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
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。
法律信息
使用涉及的专利号：US 6307087；EP 1097158；JP 5758844；CA 2336691
WGK
WGK 3
闪点(°F)
Not applicable
闪点(°C)
Not applicable
Pd-catalyzed Suzuki?Miyaura reactions of aryl halides using bulky biarylmonophosphine ligands
Altman, Ryan A., and Stephen L. Buchwald
Nature Protocols, 2.12 (2007)
Synthesis and Suzuki-Miyaura Cross-Coupling Reactions of Potassium Boc-Protected Aminomethyltrifluoroborate with Aryl and Hetaryl Halides.
Molander GA and Shin I.
Organic Letters, 13(15), 3956-3959 (2011)
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)
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)
Pd-catalyzed Kumada-Corriu cross-coupling reactions at low temperatures allow the use of Knochel-type Grignard reagents.
Ruben Martin et al.
Journal of the American Chemical Society, 129(13), 3844-3845 (2007-03-14)
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