BIS(1,5-CYCLOOCTADIENE)NICKEL(0)

BIS(1,5-CYCLOOCTADIENE)NICKEL(0) 속성

BIS(1,5-CYCLOOCTADIENE)NICKEL(0) C화학적 특성, 용도, 생산

화학적 성질

Light yellow to Brown powder to crystal.

용도

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.

제조 방법

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.

화학 반응

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

일반 설명

Yellow crystals or yellowish green solid.

반응 프로필

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.

화재위험

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

Purification Methods

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.

BIS(1,5-CYCLOOCTADIENE)NICKEL(0) 준비 용품 및 원자재

원자재

준비 용품

BIS(1,5-CYCLOOCTADIENE)NICKEL(0) 공급 업체

공급자	전화	이메일	국가	제품 수	이점
Capot Chemical Co.,Ltd.	571-85586718 +8613336195806	sales@capotchem.com	China	29797	60
Henan Tianfu Chemical Co.,Ltd.	+86-0371-55170693 +86-19937530512	info@tianfuchem.com	China	21691	55
Hangzhou FandaChem Co.,Ltd.	008657128800458; +8615858145714	fandachem@gmail.com	China	9348	55
Nanjing ChemLin Chemical Industry Co., Ltd.	025-83697070	product@chemlin.com.cn	CHINA	3012	60
Hubei Jusheng Technology Co.,Ltd.	18871490254	linda@hubeijusheng.com	CHINA	28180	58
Chongqing Chemdad Co., Ltd	+86-023-61398051 +8613650506873	sales@chemdad.com	China	39916	58
CONIER CHEM AND PHARMA LIMITED	+8618523575427	sales@conier.com	China	47465	58
career henan chemical co	+86-0371-86658258 15093356674;	factory@coreychem.com	China	29826	58
Zhengzhou Alfa Chemical Co.,Ltd	+8618530059196	sale04@alfachem.cn	China	12468	58
Hubei Ipure Biology Co., Ltd	+8613367258412	ada@ipurechemical.com	China	10326	58

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