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Kimura M, Matsuo S, Shibata K, et al. Nickel(0)-Catalyzed Three-Component Connection Reaction of Dimethylzinc, 1,3-Dienes, and Carbonyl Compounds. Angew Chem Int Ed Engl. 1999;38(22):3386-3388doi: 10.1002/(sici)1521-3773(19991115)38:22<3386::aid-anie3386>3.0.co;2-w.
Kimura, M., Matsuo, S., Shibata, K., & Tamaru, Y. (1999). Nickel(0)-Catalyzed Three-Component Connection Reaction of Dimethylzinc, 1,3-Dienes, and Carbonyl Compounds. Angewandte Chemie (International ed. in English), 38(22), 3386-3388. https://doi.org/10.1002/(sici)1521-3773(19991115)38:22<3386::aid-anie3386>3.0.co;2-w
Kimura, et al. "Nickel(0)-Catalyzed Three-Component Connection Reaction of Dimethylzinc, 1,3-Dienes, and Carbonyl Compounds." Angewandte Chemie (International ed. in English) vol. 38,22 (1999): 3386-3388. doi: https://doi.org/10.1002/(sici)1521-3773(19991115)38:22<3386::aid-anie3386>3.0.co;2-w
Kimura M, Matsuo S, Shibata K, Tamaru Y. Nickel(0)-Catalyzed Three-Component Connection Reaction of Dimethylzinc, 1,3-Dienes, and Carbonyl Compounds. Angew Chem Int Ed Engl. 1999 Nov 15;38(22):3386-3388. doi: 10.1002/(sici)1521-3773(19991115)38:22<3386::aid-anie3386>3.0.co;2-w. PMID: 10602204.
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Angew Chem Int Ed Engl. 1999 Nov 15;38(22):3386-3388. doi: 10.1002/(sici)1521-3773(19991115)38:22<3386::aid-anie3386>3.0.co;2-w.

Nickel(0)-Catalyzed Three-Component Connection Reaction of Dimethylzinc, 1,3-Dienes, and Carbonyl Compounds.

Angewandte Chemie (International ed. in English)

Kimura, Matsuo, Shibata, Tamaru

Affiliations

  1. Department of Applied Chemistry, Faculty of Engineering, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8521 (Japan).

PMID: 10602204 DOI: 10.1002/(sici)1521-3773(19991115)38:22<3386::aid-anie3386>3.0.co;2-w

Abstract

Linear 1:1:1 coupling of dimethylzinc, 1,3-dienes, and carbonyl compounds in this order is facilitated by catalytic amounts of [Ni(acac)(2)] to give (E)-3-hexen-1-ols in good yields under mild conditions [Eq. (a)]. Increasing steric hindrance at the carbonyl group favors formation of the 1:2:1 adduct, and this is the sole product when the carbonyl compound is acetone. acac=acetylacetonate.

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