Synlett 2014; 25(3): 417-422
DOI: 10.1055/s-0033-1340290
letter
© Georg Thieme Verlag Stuttgart · New York

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

Xing-Feng Bai
a   Key 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
b   State 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
a   Key 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
a   Key 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
a   Key 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*
a   Key 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
b   State 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*
a   Key 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
b   State 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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Publikationsverlauf

Received: 16. September 2013

Accepted after revision: 17. Oktober 2013

Publikationsdatum:
04. Dezember 2013 (online)


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.

Supporting Information

 
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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): νmax = 3412, 3059, 3025, 3000, 2957, 2931, 2853, 2835, 1653, 1608, 1510, 1493, 1448, 1302, 1250, 1178, 1150, 1034, 971, 830, 700, 560 cm–1.