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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:
Molecular Weight:
1013.88
MDL number:
UNSPSC Code:
12161600
PubChem Substance ID:
NACRES:
NA.22

form

solid

Quality Level

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

Application

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

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

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

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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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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The major research thrust in Professor Liming Zhang’s group is homogeneous gold catalysis ranging from discovery of novel reactivities, design of new ligands, development of versatile synthetic methods and application in natural product synthesis.

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