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804215

Sigma-Aldrich

[Ir{dFCF3ppy}2(bpy)]PF6

Synonym(s):

[Ir[dF(CF3)2ppy]2(bpy)]PF6

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About This Item

Empirical Formula (Hill Notation):
C34H18F16IrN4P
CAS Number:
Molecular Weight:
1009.70
MDL number:
UNSPSC Code:
12161600
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

form

powder

Quality Level

reaction suitability

core: iridium
reagent type: catalyst
reaction type: Photocatalysis

photocatalyst activation

450 nm

SMILES string

FP(F)(F)(F)F.FC1=CC(F)=C(C2=[N]3C=C(C(F)(F)F)C=C2)C([Ir+]345([N]6=C(C7=CC=CC=[N]75)C=CC=C6)[N]8=C(C9=C(F)C=C(F)C=C94)C=CC(C(F)(F)F)=C8)=C1.[F-]

InChI

1S/2C12H5F5N.C10H8N2.F5P.FH.Ir/c2*13-8-2-3-9(10(14)5-8)11-4-1-7(6-18-11)12(15,16)17;1-3-7-11-9(5-1)10-6-2-4-8-12-10;1-6(2,3,4)5;;/h2*1-2,4-6H;1-8H;;1H;/q;;;;;+1/p-1

InChI key

DZIQZTFRUCLPRL-UHFFFAOYSA-M

Application

When used in tandem with a nickel catalyst, the above photoredox catalyst effects the cross-coupling of C-sp3 hybridized trifluoroborates with aryl bromides under exceptionally mild conditions.

Product can be used with our line of photoreactors: Including Penn PhD (Z744035) & SynLED 2.0 (Z744080)

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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John C Tellis et al.
Science (New York, N.Y.), 345(6195), 433-436 (2014-06-07)
The routine application of C(sp3)-hybridized nucleophiles in cross-coupling reactions remains an unsolved challenge in organic chemistry. The sluggish transmetalation rates observed for the preferred organoboron reagents in such transformations are a consequence of the two-electron mechanism underlying the standard catalytic

Articles

Effective Csp2- and Csp-hybridized coupling reactions established for catalysis, expanding to multi-step Csp3-coupling.

Effective Csp2- and Csp-hybridized coupling reactions established for catalysis, expanding to multi-step Csp3-coupling.

Effective Csp2- and Csp-hybridized coupling reactions established for catalysis, expanding to multi-step Csp3-coupling.

Effective Csp2- and Csp-hybridized coupling reactions established for catalysis, expanding to multi-step Csp3-coupling.

Related Content

The central theme of the Molander group's research is the development of new synthetic methods and their application to the synthesis of organic molecules.

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    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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