Deoxygenative silylation of aromatic carbonyl compounds with HSiCl3 in the presence of quaternary phosphonium chloride: A facile route to arylmethyltrichlorosilane

Joon Soo Han; Seung-Hyun Kang; Il Nam Jung; Bok Ryul Yoo

Journal of Industrial and Engineering Chemistry, Vol.42, 157-161, October, 2016

DOI10.1016/j.jiec.2016.08.015 Export Citation

Deoxygenative silylation of aromatic carbonyl compounds with HSiCl3 in the presence of quaternary phosphonium chloride: A facile route to arylmethyltrichlorosilane

Joon Soo Han , Seung-Hyun Kang, Il Nam Jung, and Bok Ryul Yoo^†

Organosilicon Chem. Lab., Korea Institute of Science & Technology, Hwarangno 14-gil 5, Seongbuk-gu, Seoul 130-650, Republic of Korea

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Aromatic carbonyl compounds such as aromatic aldehydes and ketones [R1R2C=O: R1=H; R2=Ph (1a), 2,4-Cl2Ph (1b), 2,4-Me2Ph (1c): R1=Ph; R2=Ph (1d), 4-ClPh (1e), 4-MePh (2f), 2,4-Me2Ph (1g) undergo the deoxygenative silylation with HSiCl3 in the presence of Bu4PCl at 150 °C within 1.0-1.5 h to give arylmethyltrichlorosilanes 2 (R1R2CH-SiCl3) in high yields (85-95%). The reactivity of aromatic carbonyl compounds decreases with increasing the electron withdrawing ability of substituent(s) on the benzenering. A highly efficient synthetic route to arylmethyltrichlorosilanes has been developed starting from aromatic aldehydes and ketones in this study.

Keywords:Trichlorosilane;Aromatic carbonyl compounds;Arylmethyltrichlorosilane;Si-C coupling;Deoxygenative silylation

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Jung DE, Han JS, Yoo BR, Bull. Korean Chem. Soc., 34, 3805 (2013)
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Okamoto M, Kiya H, Yamashita H, Suzuki E, Chem. Commun., 1634 (2002)
Xu Z, Huang WS, Zhang J, Xu LW, Synthesis, 47, 3645 (2015)
Do Y, Han J, Rhee YH, Park J, Adv. Synth. Catal., 353, 3363 (2011)
Sattler W, Ruccolo S, Chaijan MR, Allah TB, Parkin G, Organometallics, 34, 4717 (2015)
Zheng J, Castro LCM, Roisnel T, Darcel C, Sortais JB, Inorg. Chim. Acta., 380, 301 (2012)
Huang L, Wang W, Wei X, Wei H, J. Phys. Chem. A, 119, 3789 (2015)
Mimoun H, J. Org. Chem., 64, 2582 (1999)
Yoo BR, Han JS, Curr. Org. Chem., 15, 2743 (2011)
Kang SH, Han JS, Lim WC, Jung IN, Lee ME, Yoo BR, Organometallics, 25, 318 (2006)
Kang SH, Han JS, Lee ME, Yoo BR, Jung IN, Organometallics, 22, 2551 (2003)
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[Related Articles]

[1] Noll W, Chemistry and Technology of Silicones, Academic, New York, 1968.

[2] Clarson SJ, Smith SD, Owen MJ, Silicones and Silicone-Modified Materials, American Chemical Society, Washington, DC, 2000.

[3] Jung DE, Han JS, Yoo BR, Bull. Korean Chem. Soc., 34, 3805 (2013)

[4] Lee DW, Yoo BR, J. Ind. Eng. Chem., 38, 1 (2016)

[5] Sanchez C, Julian B, Belleville P, Popall M, J. Mater. Chem., 15, 3559 (2005)

[6] Ghanbari A, Attat MM, J. Ind. Eng. Chem., 23, 145 (2015)

[7] Pouranfard AR, Mowla D, Esmaeilzadeh F, J. Ind. Eng. Chem., 20(2), 633 (2014)

[8] Marciniac B, Hydrosilylation: A Comprehensive Review on Recent Advances, Springer, 2009.

[9] Okamoto M, Kiya H, Yamashita H, Suzuki E, Chem. Commun., 1634 (2002)

[10] Xu Z, Huang WS, Zhang J, Xu LW, Synthesis, 47, 3645 (2015)

[11] Do Y, Han J, Rhee YH, Park J, Adv. Synth. Catal., 353, 3363 (2011)

[12] Sattler W, Ruccolo S, Chaijan MR, Allah TB, Parkin G, Organometallics, 34, 4717 (2015)

[13] Zheng J, Castro LCM, Roisnel T, Darcel C, Sortais JB, Inorg. Chim. Acta., 380, 301 (2012)

[14] Huang L, Wang W, Wei X, Wei H, J. Phys. Chem. A, 119, 3789 (2015)

[15] Mimoun H, J. Org. Chem., 64, 2582 (1999)

[16] Yoo BR, Han JS, Curr. Org. Chem., 15, 2743 (2011)

[17] Kang SH, Han JS, Lim WC, Jung IN, Lee ME, Yoo BR, Organometallics, 25, 318 (2006)

[18] Kang SH, Han JS, Lee ME, Yoo BR, Jung IN, Organometallics, 22, 2551 (2003)

[19] Magano J, Dunetz JR, Org. Process Res. Dev., 16, 1156 (2012)

[20] Sommer LH, Whitmore FC, J. Am. Chem. Soc., 68, 485 (1946)

[21] Golovkin AA, Mudrova NA, Krasnova TL, Serebrenniko LV, Nikitin VS, Chernyshev EA, Zh. Obshch. Khim., 55, 2802 (1985)

[22] Rodziewicz W, Prejzner J, Michalowski Z, Rocz. Chem., 34, 483 (1960)

[23] Benkeser RA, Smith WE, J. Am. Chem. Soc., 91, 1556 (1969)

[24] Yoo BR, Kim JH, Cho BG, Jung IN, J. Organomet. Chem., 631, 36 (2001)

[25] Benkeser R, Snyder DC, J. Organomet. Chem., 225, 107 (1982)

[26] Snyder DC, J. Organomet. Chem., 301, 137 (1986)

[27] Cho YS, Kang SH, Han JS, Yoo BR, Jung IN, J. Am. Chem. Soc., 123(23), 5584 (2001)

[28] Chult C, Corriu RJP, Reye C, Young JC, Chem. Rev., 93, 1371 (1993)

[29] Corriu RJP, Guerin C, Henner B, Wang Q, Organometallics, 10, 2297 (1991)

[30] Kira M, Sato K, Sakurai H, J. Org. Chem., 52, 948 (1987)

[31] Becker B, Corriu RJP, Guerin C, Henner B, Wang Q, J. Organomet. Chem., 368, C25 (1989)

[32] Corriu RJP, Guerin C, Henner BJL, Wang Q, Organometallics, 10, 3574 (1991)

[33] Fujita M, Hiyama T, J. Am. Chem. Soc., 106, 4629 (1984)

[34] Fujita M, Hiyama T, J. Org. Chem., 53, 5405 (1988)

[35] Boyer J, Corriu RJP, Perz R, Reye C, Tetrahedron, 37, 2165 (1981)

[36] Corriu RJP, Perz R, Reye C, Tetrahedron, 39, 999 (1983)

[37] Yang D, Tanner DD, J. Org. Chem., 51, 2267 (1986)

[38] Kohra S, Hayashida H, Tominaga Y, Hosomi A, Tetrahedron Lett., 29, 89 (1988)

[39] Patai S, Rappoport Z (Eds.), The Chemistry of Organic Silicon Compounds Part 2, Wiley, New York, 1989, pp. 1499-1515.

[40] Marciniec B, Comprehensive Handbook on Hydrosilylation, Oxford, Pergamon, 1992.

[41] Baldwin SW, Haut SA, J. Org. Chem., 40, 3885 (1975)

[42] Dear REA, J. Org. Chem., 33, 3959 (1968)