(EtO)3SiH-Promoted Palladium-Catalyzed Isomerization of Olefins: Convenient Synthesis of Internal Alkenes from Terminal Alkenes

Xing-Feng Bai; Tao Song; Wen-Hui Deng; Yun-Long Wei; Li Li; Chun-Gu Xia; Li-Wen Xu

doi:10.1055/s-0033-1340290

Synlett, Table of Contents

Synlett 2014; 25(3): 417-422
DOI: 10.1055/s-0033-1340290

letter

(EtO)₃SiH-Promoted Palladium-Catalyzed Isomerization of Olefins: Convenient Synthesis of Internal Alkenes from Terminal Alkenes

Xing-Feng Bai

^aKey Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, College of Material, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou 310012, P. R. of China Fax: +(86)57128868918 Email: liwenxu@hznu.edu.cn Email: licpxulw@yahoo.com

^bState Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics and University of Chinese Academy of Sciences, Chinese Academy of Sciences, Lanzhou 730000, P. R. of China

,

Tao Song

^aKey Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, College of Material, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou 310012, P. R. of China Fax: +(86)57128868918 Email: liwenxu@hznu.edu.cn Email: licpxulw@yahoo.com

,

Wen-Hui Deng

^aKey Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, College of Material, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou 310012, P. R. of China Fax: +(86)57128868918 Email: liwenxu@hznu.edu.cn Email: licpxulw@yahoo.com

,

Yun-Long Wei

^aKey Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, College of Material, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou 310012, P. R. of China Fax: +(86)57128868918 Email: liwenxu@hznu.edu.cn Email: licpxulw@yahoo.com

,

Li Li*

^aKey Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, College of Material, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou 310012, P. R. of China Fax: +(86)57128868918 Email: liwenxu@hznu.edu.cn Email: licpxulw@yahoo.com

,

Chun-Gu Xia

^bState Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics and University of Chinese Academy of Sciences, Chinese Academy of Sciences, Lanzhou 730000, P. R. of China

,

Li-Wen Xu*

^aKey Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, College of Material, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou 310012, P. R. of China Fax: +(86)57128868918 Email: liwenxu@hznu.edu.cn Email: licpxulw@yahoo.com

^bState Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics and University of Chinese Academy of Sciences, Chinese Academy of Sciences, Lanzhou 730000, P. R. of China

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Abstract

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Abstract

The catalytic activity of an in situ forming palladium catalyst system generated from PdCl₂(PPh₃)₂ and hydrosilane [(EtO)₃SiH] was revealed in the one-carbon migration and isomerization of 4,4-biaryl-substituted 1-butenes, in which the (EtO)₃SiH plays a key role in the palladium-catalyzed one-carbon migration and subsequent isomerization of terminal alkenes. This catalytic protocol is applied in the synthesis of a key building block of cassumunin C in high yield and promising selectivity.

Key words

olefin - palladium - isomerization - cassumunin - organosilicon

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References

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20 Typical Procedure for the Palladium-Catalyzed Isomerization 4,4-Diarylbut-1-enes (0.5 mmol), (EtO)₃SiH (0.1 mmol, 18.5 μL, 0.2 equiv) and a catalytic amount of Pd(Ph₃P)₂Cl₂ (0.005 mmol, 1 mol%) were added to a dry tube, and then the mixture was solved with dry THF (1 mL). The resulting mixture was stirred at 60 °C for 10 h. The mixture was then cooled to r.t., quenched by the addition of H₂O, and extracted by the addition of CH₂Cl₂. The organic layer was washed with H₂O, dried over Na₂SO₄, and concentrated. The residue was purified by flash column chromatography to give corresponding 4,4-diarylbut-1-enes. All the products were confirmed by GC–MS, NMR and IR spectrosopy. These data are provided in the Supporting Information. Analytical Data for 1-Methyl-2-(1-phenylbut-2-enyl)benzene (3a) ¹H NMR (400 MHz, CDCl₃): δ = 7.32 (t, J = 6.8 Hz, 2 H), 7.23 (J = 6.8 Hz, 3 H), 7.14 (d, J = 6.8 Hz, 2 H), 6.87 (d, J = 6.8 Hz, 2 H), 5.94 (dd, J = 13.6, 7.6 Hz, 1 H), 5.74–5.68 (m, 0.14 H), 5.47 (dq, J = 14.8, 6.4 Hz, 0.88 H), 5.02 (d, J = 9.6 Hz, 0.14 H), 4.66 (d, J = 7.2 Hz, 0.86 H), 3.81 (s, 3 H), 1.77 (d, J = 6.4 Hz, 3 H) ppm. ¹³C NMR (100 MHz, CDCl₃): δ = 158.0, 144.6, 136.5, 133.9, 129.5, 128.5, 128.3, 126.7, 126.1, 113.8, 55.3, 53.3, 18.0 ppm. GC–MS: m/z calcd for C₁₇H₁₈ [M]⁺: 222.3; found: 222.1. IR (KBr): ν_max = 3412, 3059, 3025, 3000, 2957, 2931, 2853, 2835, 1653, 1608, 1510, 1493, 1448, 1302, 1250, 1178, 1150, 1034, 971, 830, 700, 560 cm^–1.

Supplementary Material

Supporting Information