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763233

Sigma-Aldrich

[2-(Dicyclohexylphosphino)-3,6-dimethoxy-2′,4′,6′-triisopropyl-1,1′-biphenyl]gold(I) bis(trifluoromethanesulfonyl)imide

Synonym(s):

BrettPhos AuNTf2

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About This Item

Empirical Formula (Hill Notation):
C37H53AuF6NO6PS2
CAS Number:
1296269-97-0
Molecular Weight:
1013.88
MDL number:
MFCD22572681
UNSPSC Code:
12161600
PubChem Substance ID:
329767037
NACRES:
NA.22

form

solid

Quality Level

100

reaction suitability

core: gold
reaction type: Cross Couplings
reagent type: catalyst

mp

192-209 °C (decomposition)

SMILES string

FC(F)(F)S(=O)(=O)N([Au])S(=O)(=O)C(F)(F)F.COc1ccc(OC)c(c1P(C2CCCCC2)C3CCCCC3)-c4c(cc(cc4C(C)C)C(C)C)C(C)C

InChI

1S/C35H53O2P.C2F6NO4S2.Au/c1-23(2)26-21-29(24(3)4)33(30(22-26)25(5)6)34-31(36-7)19-20-32(37-8)35(34)38(27-15-11-9-12-16-27)28-17-13-10-14-18-28;3-1(4,5)14(10,11)9-15(12,13)2(6,7)8;/h19-25,27-28H,9-18H2,1-8H3;;/q;-1;+1

InChI key

SMTGSBLIUQSWAP-UHFFFAOYSA-N

Related Categories

Application

Bulky gold pi-acid catalyst used in oxidative cyclization reactions.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Youliang Wang et al.
Angewandte Chemie (International ed. in English), 52(30), 7795-7799 (2013-06-22)
Golden aryne? Gold aryne complexes are inferred as transition states in dual gold-catalyzed cyclizations of cis-enediynes (see scheme; DCE = 1,2-dichloroethane). They are better described as ortho-aurophenyl cations, which react with weak nucleophiles and undergo facile intramolecular insertions into C(sp(3))-H

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