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表单
powder
质量水平
反应适用性
core: palladium
reaction type: Trost Asymmetric Allylic Alkylation
reaction type: Tsuji-Trost Reaction
reagent type: catalyst
环保替代产品特性
Catalysis
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颜色
faint beige to dark beige-brown
环保替代产品分类
SMILES字符串
CC(C)(C)[C@@H]1[N]([Pd]23C4([H])=C3([H])C(OC4=O)=O)=C(C5=CC=CC=C5[P]2(C6=CC=CC=C6)C7=CC=CC=C7)OC1
InChI
InChI=1S/C25H26NOP.C4H2O3.Pd/c1-25(2,3)23-18-27-24(26-23)21-16-10-11-17-22(21)28(19-12-6-4-7-13-19)20-14-8-5-9-15-20;5-3-1-2-4(6)7-3;/h4-17,23H,18H2,1-3H3;1-2H;/q;;-1/p+1/t23-;;/m1../s1
InChI key
FGSJOEKZZULTLF-MQWQBNKOSA-O
一般描述
(S)-tBuPHOX-Pd-MAH is a chiral Pd(0) precatalyst first produced in the group of David C. Leitch for asymmetric allylic alkylation reactions. The complex bears a chiral Pfaltz-Helmchen-Williams (PHOX) ligand as well as an easily diplaced maleic anhydride (MAH) ligand.
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应用
Suitable for use in asymmetric allylic alkylation reactions such as the Tsuji–Trost reaction/Trost asymmetric allylic alkylation reaction. https://www.sigmaaldrich.com/US/en/technical-documents/technical-article/chemistry-and-synthesis/cross-coupling/trost-ligands https://www.sigmaaldrich.com/US/en/technical-documents/technical-article/chemistry-and-synthesis/cross-coupling/phox
特点和优势
(S)-tBuPHOX-Pd-MAH is a rare example of a chiral, isolable Pd(0) precatalyst for allylic alkylation reactions. Using a chiral single-component precatalyst instead of forming the chiral catalytic speices in-situ avoids activity, reproducibility, and/or selectivity problems arising from incomplete formation of the desired chiral catalyst.
相关产品
储存分类代码
11 - Combustible Solids
WGK
WGK 3
闪点(°F)
Not applicable
闪点(°C)
Not applicable
Jingjun Huang et al.
Nature communications, 14(1), 8058-8058 (2023-12-06)
Stereoselective carbon-carbon bond formation via palladium-catalyzed asymmetric allylic alkylation is a crucial strategy to access chiral natural products and active pharmaceutical ingredients. However, catalysts based on the privileged Trost and Pfaltz-Helmchen-Williams PHOX ligands often require high loadings, specific preactivation protocols
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