Nickel(0)-catalyzed couplings of vinyl- alanes and -zirconocenes with chloromethylated heteroaromatics: A route to E-allylated heterocycles

Tetrahedron

Volumn 54, Issue 25, 1998, Pages 6999-7012

  Lipshutz, Bruce H ^a   Kim, Sung Kyu ^a   Mollard, Paul ^a   Blomgren, Peter A ^a   Stevens, Kirk L ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; VINYL DERIVATIVE;

ANTIMICROBIAL ACTIVITY; ARTICLE; CATALYSIS; DRUG STRUCTURE; DRUG SYNTHESIS; METAL BINDING; METHODOLOGY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0032543627     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00342-1     Document Type: Article

References (31)

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8. 3. Lipshutz, B.H.; Bulow, G.; Lowe, R.F.; Stevens, K.L. J. Am. Chem. Soc., 1996, 118, 5512; for earlier related coupings with benzylic systems and Pd(0), see Negishi, E.I.; Matsushita, H.; Okukado, N. Tetrahedron Lett. 1981, 22, 2715.
9. 3. Lipshutz, B.H.; Bulow, G.; Lowe, R.F.; Stevens, K.L. J. Am. Chem. Soc., 1996, 118, 5512; for earlier related coupings with benzylic systems and Pd(0), see Negishi, E.I.; Matsushita, H.; Okukado, N. Tetrahedron Lett. 1981, 22, 2715.
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13. 3 complex could be used interchangeably with identical results.
14. 6. Alternatively and experimentally simpler, the vinylalane could be first combined with the heterocyclic substrate to which was then added the Ni(0) catalyst; no difference was noted in yields.
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25. 3 was omitted gave comparable yields of product in each case.
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31. 16. This alcohol was obtained from Dr. Ioannis Houpis at Merck & Co, Process Research, Rahway, N.J. It was used as received en route to the chlormethyl derivative described in the Experimental Section.