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Sigma-Aldrich

三(二亚苄基丙酮)二钯(0)

97%

同義詞:

Pd2dba3, Pd2(dba)3

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About This Item

線性公式:
(C6H5CH=CHCOCH=CHC6H5)3Pd2
CAS號碼:
分子量::
915.72
MDL號碼:
分類程式碼代碼:
12161600
PubChem物質ID:
NACRES:
NA.22
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品質等級

化驗

97%

形狀

powder

反應適用性

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

mp

152-155 °C (lit.)

SMILES 字串

[Pd].[Pd].O=C(\C=C\c1ccccc1)/C=C/c2ccccc2.O=C(\C=C\c3ccccc3)/C=C/c4ccccc4.O=C(\C=C\c5ccccc5)/C=C/c6ccccc6

InChI

1S/3C17H14O.2Pd/c3*18-17(13-11-15-7-3-1-4-8-15)14-12-16-9-5-2-6-10-16;;/h3*1-14H;;/b3*13-11+,14-12+;;

InChI 密鑰

CYPYTURSJDMMMP-WVCUSYJESA-N

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相關類別

一般說明

三(二亚苄基丙酮)二钯(0)(Pd2(dba)3)是一种多功能化合物,广泛用作各种Pd介导转化反应的Pd(0)源。[1]众所周知,Pd2(dba)3反应性高,可促进氧化加成反应。它是由钯盐与二亚苄基丙酮配体反应制得。它可作为Suzuki交叉偶联、Heck偶联、芳基化、Buchwald-Hartwig胺化和氟化等多种反应的催化剂。它通常以催化量使用,已被证明可有效促进芳基卤化物和硼酸之间的偶联反应。[2]

对于小规模和高通量应用,可选用ChemBeads(919772

應用

    钯催化交叉偶联反应应用指南

    作为反应物参与:

    • 合成氮杂环庚烷[3]
    • 与白磷相互作用合成纳米磷化钯
    • 制备三苯基膦羰基钯簇络合物
    • 作为前驱体合成可用作Heck偶联反应催化剂的功能化多壁碳纳米管-钯配合物
    • 通过在炔烃上添加S-S键和S-H键选择性形成碳硫键


    作为催化剂用于:

    • Suzuki交叉偶联反应
    • PCN和PCS钳形钯配合物催化的串联烯丙基化
    • 芳基氯化物Suzuki偶联催化剂[4](式1)
    • 芳基氯化物Heck偶联催化剂[4](式2)
    • 酮类芳基化催化剂[5](式3)
    • 芳基卤化物Buchwald-Hartwig胺化催化剂[6](式4)
    • 烯丙基氯化物氟化催化剂[7](式5)
    • 羧酸酯β-芳基化催化剂[8](式6)
    • 1,1-二氯-1-烯烃羰基化催化剂[9](式7)
    • 芳基和乙烯基三氟甲磺酸酯转化为芳基和乙烯基卤化物的催化剂[10](式8)
    • 对映选择性Tsuji烯丙基化的钯源[11][12]

象形圖

Exclamation markEnvironment

訊號詞

Warning

危險聲明

危險分類

Aquatic Chronic 2 - Skin Sens. 1

儲存類別代碼

11 - Combustible Solids

水污染物質分類(WGK)

WGK 2

閃點(°F)

Not applicable

閃點(°C)

Not applicable

個人防護裝備

Eyeshields, Gloves, type N95 (US)


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分析證明 (COA)

Lot/Batch Number

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存取文件庫

Tetrahedron Letters, 33, 4859-4859 (1992)
European Journal of Organic Chemistry, 10, 2214-2222 (2004)
The Reaction Mechanism of the Enantioselective Tsuji Allylation: Inner-Sphere and Outer-Sphere Pathways, Internal Rearrangements, and Asymmetric C?C Bond Formation
John A. Keith, Douglas C. Behenna, et al.
Journal of the American Chemical Society, 134(46) , 19050?19060-19050?19060 (2012)
Catalysts for Suzuki?Miyaura Coupling Processes:? Scope and Studies of the Effect of Ligand Structure
Timothy E. Barder, Shawn D. Walker, Joseph R. Martinelli, and Stephen L. Buchwald
Journal of the American Chemical Society, 127(13), 4685?4696-4685?4696 (2005)
Crystal and molecular structure of tris (dibenzylideneacetone) dipalladium (0).
Pierpont CG and Mazza MC
Inorganic Chemistry, 13(8), 1891-1895 (1974)

文章

JosiPhos CyPF-tBu and palladium give catalyst for alkoxylation of activated heteroaryl halides with primary, secondary, and tertiary alcohols

Heck反应是烯烃与芳基或乙烯基卤化物(或三氟甲磺酸酯)之间的钯催化交叉偶联反应,用于生成取代的烯烃。

Questions

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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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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    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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