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ALD00508

Sigma-Aldrich

Yu Fluorination Ligand

≥95%

Synonym(s):

2,5,6,8-tetramethyl-3,4-dihydro-2H-pyrano[2,3-b]quinoline

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About This Item

Empirical Formula (Hill Notation):
C16H19NO
CAS Number:
1771764-64-7
Molecular Weight:
241.33
UNSPSC Code:
41116155
PubChem Substance ID:
329772697
NACRES:
NA.22

Quality Level

100

Assay

≥95%

form

powder

reaction suitability

reagent type: catalyst
reagent type: ligand
reaction type: C-H Activation

SMILES string

CC1=C2C(OC(C)CC2)=NC3=C1C(C)=CC(C)=C3

InChI

1S/C16H19NO/c1-9-7-10(2)15-12(4)13-6-5-11(3)18-16(13)17-14(15)8-9/h7-8,11H,5-6H2,1-4H3

InChI key

LOKRNFHHPZEJLL-UHFFFAOYSA-N

Related Categories

General description

Yu Fluorination Ligand is widely employed for the chemoselective functionalization of sp2- and sp3 C-H bonds.

Application

The Yu Fluorination Ligand in tandem with Selectfluor(R) (Aldrich 439479) under palladium catalysis can promote direct fluorination of C(sp3)-H bonds stereoselectively. Yu and coworkers have displayed this on amino acid derivatives with directing group assistance from the Yu-Wasa Auxiliary (Aldrich 791806).

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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Related Content

Yu Group – Professor Product Portal

The Yu program centers around the discovery of catalytic carbon–carbon and carbon–heteroatom bond forming reactions based on C–H activation. Target transformations are selected to enable 1) the use of simple and abundant starting materials such as aliphatic acids, amines and alcohols, and 2) disconnections that drastically shorten the synthesis of a drug molecule or a major class of biologically active compounds.

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