ビス(シクロオクタジエン)ニッケル

危険有害性情報のコード(GHS)

• 絵表示(GHS)

  

• 注意喚起語

  Danger

• 危険有害性情報

  H228：可燃性固体

  H317：アレルギー性皮膚反応を起こすおそれ

  H351：発がんのおそれの疑い

  H372：長期にわたる、または反復暴露により臓器の障 害

• 注意書き

  P201：使用前に取扱説明書を入手すること。

  P202：全ての安全注意を読み理解するまで取り扱わないこ と。

  P210：熱/火花/裸火/高温のもののような着火源から遠ざ けること。－禁煙。

  P280：保護手袋/保護衣/保護眼鏡/保護面を着用するこ と。

  P302+P352：皮膚に付着した場合：多量の水と石鹸で洗うこと。

  P308+P313：暴露または暴露の懸念がある場合：医師の診断/手当てを 受けること。

ビス(シクロオクタジエン)ニッケル 価格

ビス(シクロオクタジエン)ニッケル 化学特性,用途語,生産方法

• 外観

  微黄色～黄色、結晶～結晶性粉末

• 用途

  触媒。

• 用途

  有機合成用触媒

• 特徴

  近似的D2d対称，Niは四つの二重結合と四面体形結合，Ni－C 211～214 pm (125 K)

  

• 使用上の注意

  不活性ガス封入

• 化学的特性

  Light yellow to Brown powder to crystal.

• 使用

  Bis(1,5-cyclooctadiene)nickel(0) is used as a catalyst for the cycloaddition of 1,3-dienes and is used to catalyze the addition of allyl phenyl sulfide to alkynes leading to 1,4-dienes. Also, it is involved as a catalyst for asymmetric alpha-arylation and heteroarylation of ketones with chloroarenes, stereoselective borylative ketone-diene coupling, cycloaddition of benzamides with internal alkynes and methyl carboxylation of homopropargylic alcohols.

• 製造方法

  Bis(1,5-cyclooctadiene)nickel(0) is prepared by reduction of anhydrous nickel(II) acetylacetonate in the presence of the diolefin:
  Ni(acac)2 + 2 cod + 2 AlEt3 → Ni(cod)2 + 2 acacAlEt2 + C2H6 + C2H4
  Ni(cod)2 is moderately soluble in several organic solvents. One or both 1,5-cyclooctadiene ligands are readily displaced by phosphines, phosphites, bipyridine, and isocyanides. If exposed to air, the solid oxidizes to nickel(II) oxide. As a result, this compound is generally handled in a glovebox.

• 反応性

  Catalyst for Grignard metathesis chain-growth polymerization of Poly(bithienylmethylene)s
  Catalyst for neopentylglycolborylation of ortho-substituted aryl halides
  Catalyst for Suzuki-Miyaura coupling reactions of heteroaryl ethers with arylboronic acids
  Catalyst for carboxylation of naphthyl pivalates with CO2
  Catalyst decarboxylative C?P cross-coupling of alkenyl acids with P(O)H compounds
  Catalyst for direct amination of phenols via C–O Bond Activation using 2,4,6-Trichloro-1,3,5-triazine as reagent
  Catalyst for conversion of aryl, heteroaryl and pharmaceutically relevant chlorides to the corresponding trifluoromethyl sulphides
  Catalytic precursor for Suzuki–Miyaura cross-coupling reactions in water under very mild reaction conditions: (a) aryl–heteroaryl cross-couplings; (b) Hetero–heteroaryl cross-couplings
  
  

• 一般的な説明

  Yellow crystals or yellowish green solid.

• 反応プロフィール

  BIS(1,5-CYCLOOCTADIENE)NICKEL(0) is extremely air and moisture sensitive. BIS(1,5-CYCLOOCTADIENE)NICKEL(0) is sensitive to exposure to light. BIS(1,5-CYCLOOCTADIENE)NICKEL(0) is incompatible with oxidizing agents, acids and acid fumes.

• 火災危険

  Flash point data for BIS(1,5-CYCLOOCTADIENE)NICKEL(0) are not available. BIS(1,5-CYCLOOCTADIENE)NICKEL(0) is probably combustible.

• 純化方法

  It is available in sealed ampoules under N2. All procedures should be carried out in a dry box and in an atmosphere of N2 or Argon in subdued light because the complex is light and oxygen sensitive, and flammable. The solid is washed with dry Et2O (under Ar) and separates from toluene as yellow crystals. Filter this under Ar gas pressure, place the crystals in a container and dry under a vacuum of 0.01mm to remove adhered toluene, flush with Ar and seal them under Ar or N2 in glass ampoules. [Semmelhack Org Reactions 19 115 and 178 1972, Wilke et al. Justus Liebigs Ann Chem 699 1 1966, Wender & Jenkins J Am Chem Soc 111 6432 1989, Fieser & Fieser Reagents for Org Synth 4 33, 16 29, 17 32.] SUSPECTED CARCINOGEN.

• 参考文献

  P. Macchi, D.M. Proserpio, A. Sironi, J. Am. Chem. Soc., 120, 1447 (1998), DOI: 10.1021/ja972558.

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