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Merck
CN

669032

PEPPSI™-IPr 催化剂

98%, Umicore

别名:

[1,3-双(2,6-二异丙基苯基)咪唑-2-基亚基](3-氯吡啶基)二氯化钯(II)

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关于此项目

经验公式（希尔记法）:
C32H40Cl3N3Pd
化学文摘社编号:
905459-27-0
分子量:
679.46
UNSPSC Code:
12352103
PubChem Substance ID:
24884825
NACRES:
NA.22
MDL number:
MFCD08457656

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产品名称

PEPPSI™-IPr 催化剂, 98%, Umicore

SMILES string

Cl[Pd]Cl.Clc1cccnc1.CC(C)c2cccc(C(C)C)c2N3CN(C=C3)c4c(cccc4C(C)C)C(C)C

InChI

1S/C27H38N2.C5H4ClN.2ClH.Pd/c1-18(2)22-11-9-12-23(19(3)4)26(22)28-15-16-29(17-28)27-24(20(5)6)13-10-14-25(27)21(7)8;6-5-2-1-3-7-4-5;;;/h9-16,18-21H,17H2,1-8H3;1-4H;2*1H;/q;;;;+2/p-2

InChI key

BLDKGTGQENJFON-UHFFFAOYSA-L

assay

98%

reaction suitability

core: palladium
reaction type: Buchwald-Hartwig Cross Coupling Reaction
reaction type: Cross Couplings
reaction type: Heck Reaction
reaction type: Hiyama Coupling
reaction type: Negishi Coupling
reaction type: Sonogashira Coupling
reaction type: Stille Coupling
reaction type: Suzuki-Miyaura Coupling
reagent type: catalyst

manufacturer/tradename

Umicore

mp

230 °C

Quality Level

200

相关类别

Application

钯催化交叉偶联反应应用指南
  • Kumada-Tamao-Corriu（KTC） 反应的催化剂（平衡1)
  • Negishi偶联反应的催化剂 (eq.2）
  • Suzuki 偶联反应的催化剂（平衡3）
  • Buchwald-Hartwig 胺化反应的催化剂（平衡4)
PEPPSI<SUP>™</SUP>-IPr catalyst

对于小规模和高通量用途，产品为ChemBeads （931063）

General description

PEPPSI™-IPr催化剂广泛用于羰基化交叉偶联反应。

Legal Information

Umicore 产品

该产品及其制造或使用是Umicore PMC拥有或控制的一项或多项已授权或正在申请的美国专利（和国外等同产品）的主题。通过Sigma-Aldrich、其关联公司或其授权分销商从Umicore PMC购买该产品，将授予买方有限的、一次性、非独家、不可让渡、不可转让的许可。买方使用此产品可能会侵犯第三方拥有或控制的专利。买方的唯一责任是确保产品的使用不会侵犯第三方的专利权或超出本协议授权的许可范围。

如需更多产品相关信息，请在http://www.pmc.umicore.com上联系您当地的Umicore PMC负责人。

已获得专利，美国专利号7,250,510。由Total Synthesis Ltd独家授权销售。
PEPPSI is a trademark of Total Synthesis Ltd.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral

存储类别

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

历史批次信息供参考:

分析证书(COA)

Lot/Batch Number
MKCR1044
MKBX5997V
STBG1185V
STBG1186V
STBG0020V

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  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  3. Where can I find more information on the possible applications of Product 669032, PEPPSI™-IPr catalyst?

    ChemFiles 6.3 explores the advantages and reaction applications of the PEPPSI-IprTM catalyst.

  4. When using Product 669032, PEPPSI™-IPr catalyst, how can I remove any trace palladium from the reaction mixture after the reaction is complete?

    You may be interested in the QuadraPure metal scavengers, like Product No. 665422. These functionalized beads can effectively remove selected trace metallic impurities in a relatively easy process.

  5. What is the difference between Product 669032, PEPPSI™-IPr catalyst, and the ChemDose version, Product 685143?

    Both products are the same catalyst, but in different forms. Product 669032 is a powder, while 685143 is the catalyst in tablet form. A specific amount of catalyst (2μmol for 685143) is impregnated into an inert tablet matrix as a time-saving alternative to weighing out the catalyst. More information on the ChemDose tablets is found at:

  6. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

  7. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  8. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

Facile access to sterically hindered aryl ketones via carbonylative cross-coupling: application to the total synthesis of luteolin
O?Keefe BM, et al.
Tetrahedron, 67(24), 4344-4351 (2011)
Michael G Organ et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 13(1), 150-157 (2006-12-05)
An easily employed, highly versatile Kumada-Tamao-Corriu (KTC) protocol utilizing the PEPPSI (Pyridine, Enhanced, Precatalyst, Preparation, Stabilization and Initiation) precatalysts 1 and 2 is detailed. The ease-of-use of these catalysts and the synthesis of a wide range of hindered biaryls, large
Organ, M. G.; Abdel-Hadi, M. et al.
Chemistry (Weinheim An Der Bergstrasse, Germany), 150, 150-150 (2007)
Jørn Eivind Tungen et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 20(45), 14575-14578 (2014-09-17)
The first total synthesis of the lipid mediator MaR1n-3 DPA (5) has been achieved in 12 % overall yield over 11 steps. The stereoselective preparation of 5 was based on a Pd-catalyzed sp(3) -sp(3) Negishi cross-coupling reaction and a stereocontrolled Evans-Nagao acetate
Michael G Organ et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 12(18), 4749-4755 (2006-03-29)
We have developed the first user-friendly Negishi protocol capable of routinely cross-coupling all combinations of alkyl and aryl centers. The use of an easily synthesized, air stable, highly active, well-defined precatalyst PEPPSI-IPr (1; PEPPSI=pyridine-enhanced precatalyst preparation, stabilization and initiation; IPr=diisopropylphenylimidazolium
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PEPPSI™-IPent for Demanding Cross-Coupling Reactions

Professor Mike Organ and co-workers have developed the PEPPSI™ (Pyridine-Enhanced Precatalyst Preparation Stabilization and Initiation) precatalysts for palladium-catalyzed cross-coupling reactions.

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