944254
tBuSPhos
≥95%
Synonym(s):
Di-tert-butyl(2′,6′-dimethoxy-[1,1′-biphenyl]-2-yl)phosphane, [2-ditertbutylphosphino-2′,6′-dimethoxybiphenyl]
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About This Item
Empirical Formula (Hill Notation):
C22H31O2P
CAS Number:
Molecular Weight:
358.45
MDL number:
Quality Level
product line
Buchwald Ligand
assay
≥95%
form
powder, crystals or chunks
color
white to off-white
mp
139-140 °C
functional group
phosphine
SMILES string
CC(C)(C)P(C(C)(C)C)C1=C(C=CC=C1)C2=C(C=CC=C2OC)OC
InChI
InChI=1S/C22H31O2P/c1-21(2,3)25(22(4,5)6)19-15-10-9-12-16(19)20-17(23-7)13-11-14-18(20)24-8/h9-15H,1-8H3
InChI key
JJPUFWFLYXQTEU-UHFFFAOYSA-N
General description
tBuSPhos [2-ditertbutylphosphino-2′,6′-dimethoxybiphenyl] is an electron-rich biaryl phosphine ligand developed by the Buchwald group to enhance the reactivity of palladium catalysis during cross-coupling reaction.
Application
tBuSPhos has been used in:
- The Pd catalyzed amination of hindered aryl halides with 9H-carbazole
- The chemoselective Suzuki coupling of aryl chlorides bearing cidic functional groups.
- The synthesis of gold(I) carbenes from chloro(mesityl)methylgold(I) carbenoids bearing Buchwald-type ligands.
Features and Benefits
The palladium complexes of tBuSPhos exhibit high activity for Suzuki coupling reactions involving aryl chlorides, which are unreactive with palladium complexes of many other phosphine ligands.
Storage Class
11 - Combustible Solids
flash_point_f
Not applicable
flash_point_c
Not applicable
Regulatory Information
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Site-Selective Cross-Coupling of Remote Chlorides Enabled by Electrostatically Directed Palladium Catalysis
Golding W A,et.al
Journal of the American Chemical Society, 140, 13570-13574 (2018)
Expansion of the Ligand Knowledge Base for Chelating P,P-Donor Ligands (LKB-PP)
Jover J,et.al
Organometallics, 31, 5302-5306 (2012)
Palladium-Catalysed Amination of Hindered Aryl Halides with 9H-Carbazole
Ohtsuka Y,et.al
Synthetic Communications, 49, 159-165 (2019)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 944254-5G | 04065273477283 |
| 944254-1G | 04065273477276 |