Synlett 2018; 29(06): 742-746
DOI: 10.1055/s-0036-1591845
cluster
© Georg Thieme Verlag Stuttgart · New York

Ni-Catalyzed Formal Carbonyl-Ene Reaction of Terminal Alkenes via Carbon Dioxide Insertion

Yasuyuki Mori
a  Molecular Engineering Institute, Kindai University, 11-6 Kayanomori Iizuka, Fukuoka 820-8555, Japan   Email: ymori@moleng.fuk.kindai.ac.jp
,
Chieko Shigeno
b  Graduate School of Engineering, Nagasaki University, Bunkyo-machi 1-14, Nagasaki 852-8521, Japan   Email: masanari@nagasaki-u.ac.jp
,
Ying Luo
b  Graduate School of Engineering, Nagasaki University, Bunkyo-machi 1-14, Nagasaki 852-8521, Japan   Email: masanari@nagasaki-u.ac.jp
,
Bun Chan
b  Graduate School of Engineering, Nagasaki University, Bunkyo-machi 1-14, Nagasaki 852-8521, Japan   Email: masanari@nagasaki-u.ac.jp
,
Gen Onodera
b  Graduate School of Engineering, Nagasaki University, Bunkyo-machi 1-14, Nagasaki 852-8521, Japan   Email: masanari@nagasaki-u.ac.jp
,
b  Graduate School of Engineering, Nagasaki University, Bunkyo-machi 1-14, Nagasaki 852-8521, Japan   Email: masanari@nagasaki-u.ac.jp
› Author Affiliations
We gratefully acknowledge funding from the Grants-in-Aid for Scientific Research (B) (26288052) from the Ministry of Education, Culture, Sports and Technology (MEXT), Japan.
Further Information

Publication History

Received: 27 September 2017

Accepted after revision: 07 November 2017

Publication Date:
08 December 2017 (online)

Published as part of the Cluster C–C Activation

Abstract

Nickel catalyzes the multicomponent coupling reaction of terminal alkenes, carbon dioxide, and organoaluminum reagents, leading to the synthesis of homoallylic alcohols in moderate-to-good yields with excellent regio- and stereoselectivities.

Supporting Information

 
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  • 16 General Procedure for the Ni-Catalyzed Three-Component Coupling Reaction of Alkene, CO2, Organoaluminum Reagent (Table 1, Entry 4) The reaction was undertaken as follows: Into a carbon dioxide purged flask with Ni(cod)2 (13.8 mg, 0.05 mmol) and PCy3 (28.1 mg, 0.1 mmol) were introduced successively 1,4-dioxane (4 mL), allylbenzene (59.1 mg, 0.5 mmol), and Me3Al (1.5 mL of 1 M solution in n-hexane, 1.5 mmol) via syringe. The homogeneous mixture was stirred at 40 °C for 24 h, during which the reaction was monitored by TLC. Then the mixture was quenched by adding 2 N HCl (10 mL) and extracted with ethyl acetate three times. The combined organic extracts were washed with brine and then dried (MgSO4) and concentrated in vacuo. The residual oil was subjected to column chromatography over silica gel (hexane/ethyl acetate = 2:1, v/v) to give 3aa (64.3 mg, 0.36 mmol, 73%) as a pale yellow oil. (E)-2-Methyl-5-phenylpent-4-en-2-ol (3aa) TLC: Rf = 0.25 (hexane/ethyl acetate = 4:1, v/v). IR (neat): 3387 (m), 3059 (m), 2970 (s), 1599 (s), 1497 (m), 1377 (s), 1140 (s), 968 (s), 692 (s) cm–1. 1H NMR (400 MHz, CDCl3): δ = 1.27 (s, 6 H), 1.54 (br, 1 H), 2.39 (d, J = 7.6 Hz, 2 H), 6.28 (dt, J = 15.9, 7.6 Hz, 1 H), 6.46 (d, J = 15.9 Hz, 1 H), 7.21 (t, J = 7.3 Hz, 1 H), 7.30 (t, J = 7.3 Hz, 2 H), 7.34 (d, J = 7.3 Hz, 2 H). 13C NMR (100 MHz, CDCl3): δ = 29.3, 47.4, 70.9, 125.7, 126.1, 127.2, 128.5, 133.6, 137.3. HRMS: m/z calcd for C12H16O: 176.1201; found: m/z (relative intensity) = 176.1203 (9) [M+], 118 (100). (E)-2-Methyldec-4-en-2-ol (3ha) Pale yellow oil; yield 46.0 mg (0.27 mmol, 54%); TLC: Rf = 0.50 (hexane/ethyl acetate = 4:1, v/v). IR (neat): 3361 (br), 2962 (s), 2927 (s), 2856 (m), 1497 (w), 1377 (w), 1151 (w), 972 (w) cm–1. 1H NMR (400 MHz, CDCl3): δ = 0.89 (t, J = 6.8 Hz, 3 H), 1.20 (s, 6 H), 1.26–1.41 (m, 6 H), 1.50 (br, 1 H), 2.03 (q, J = 7.3 Hz, 2 H), 2.16 (d, J = 6.8 Hz, 2 H), 5.46 (dt, J = 15.1, 7.3 Hz, 1 H), 5.53 (dt, J = 15.1, 6.8 Hz, 1 H). 13C NMR (100 MHz, CDCl3): δ = 14.0, 22.5, 29.0, 29.2, 31.4, 32.7, 47.0, 70.4, 125.2, 135.4. HRMS: m/z calcd for C11H22O: 170.1671; found: m/z (relative intensity) = 170.1668 (14) [M+], 155 (100).