910724
PhPAd-DalPhos
≥95%, powder
Synonym(s):
8-(2-(Diphenylphosphaneyl)phenyl)-1,3,5,7-tetramethyl-2,4,6-trioxa-8-phosphaadamantane
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About This Item
Empirical Formula (Hill Notation):
C28H30O3P2
CAS Number:
Molecular Weight:
476.48
MDL number:
UNSPSC Code:
12352002
NACRES:
NA.22
Product Name
PhPAd-DalPhos, ≥95%
assay
≥95%
form
powder
reaction suitability
reagent type: ligand
mp
193-194 °C
functional group
phosphine
SMILES string
P4(C5(OC6(OC(OC4(C6)C)(C5)C)C)C)c1c(cccc1)P(c3ccccc3)c2ccccc2
InChI
1S/C28H30O3P2/c1-25-19-27(3)31-26(2,29-25)20-28(4,30-25)33(27)24-18-12-11-17-23(24)32(21-13-7-5-8-14-21)22-15-9-6-10-16-22/h5-18H,19-20H2,1-4H3
InChI key
SWSJANGQMCPBHH-UHFFFAOYSA-N
Application
PhPAd-DalPhos is ligand developed in the Stradiotto lab that when combined with a Ni(II) source forms an air stable precatalyst for cross coupling of aryl electrophiles with bulky primary amines.
Storage Class
13 - Non Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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Joseph P Tassone et al.
Angewandte Chemie (International ed. in English), 58(8), 2485-2489 (2019-01-04)
The base metal-catalyzed C-N cross-coupling of bulky α,α,α-trisubstituted primary alkylamines with (hetero)aryl electrophiles represents a challenging and under-developed class of transformations that is of significant potential utility, including in the synthesis of lipophilic active pharmaceutical ingredients. Herein, we report that
Christopher M Lavoie et al.
Nature communications, 7, 11073-11073 (2016-03-24)
Palladium-catalysed C(sp(2))-N cross-coupling (that is, Buchwald-Hartwig amination) is employed widely in synthetic chemistry, including in the pharmaceutical industry, for the synthesis of (hetero)aniline derivatives. However, the cost and relative scarcity of palladium provides motivation for the development of alternative, more