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Synlett 2011(20): 3031-3035  
DOI: 10.1055/s-0031-1289907
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Metal-Free Relay Oxidation: Valuable Synthesis of Acylsilane and Ketones under Aerobic Oxidation

Xing-Feng Baia, Guang Gaoa, Zhan-Jiang Zhenga, Fei Lia, Guo-Qiao Laia, Kezhi Jianga, Fuwei Lib, Li-Wen Xu*a,b
a Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Hangzhou 310012, P. R. of China
Fax: +86(571)28865135; e-Mail: liwenxu@hznu.edu.cn; e-Mail: licpxulw@yahoo.com;
b State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, P. R. of China
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Publication History

Received 18 October 2011
Publication Date:
23 November 2011 (online)

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Abstract

In this letter, an example of interesting metal-free relay air oxidation of α-hydroxysilanes, promoted by the hydroperoxidated carbonyl compounds derived from the Michael reaction of 5,5-dimethylcyclohexane-1,3-dione and chalcone, is reported. A series of aromatic acylsilanes with TBDPS were obtained in promising isolated yields. In addition, as an extension of the relay oxidation under aerobic conditions, this catalyst-free relay oxidation induced by diketone can be applied to the oxidation of general aromatic alcohols (up to 75% yield).

Key words

catalyst-free - oxidation - silane - ketone - relay chemistry

    References

  • Reviews:
  • 1a Ricci A. Degl’Innocenti A. Synthesis  1986,  647 
    Google Scholar
  • 1b Jurczak J. Golebiowski A. Chem. Rev.  1989,  89:  149 
    Google Scholar
  • 1c Page PCB. Klair SS. Rosenthal S. Chem. Soc. Rev.  1990,  19:  147 
    Google Scholar
  • 2a Corey EJ. Luo G. Lin LS. Angew. Chem. Int. Ed.  1998,  37:  1126 
    Google Scholar
  • 2b Berber H. Brigaud T. Lefebvre O. Plantier-Royon R. Portella C. Chem. Eur. J.  2001,  7:  903 
    Google Scholar
  • 2c Nicewicz DA. Satterfirld AD. Schmit DC. Johnson JS. J. Am. Chem. Soc.  2008,  130:  17281 
    Google Scholar
  • 2d Behenna DC. Corey EJ. J. Am. Chem. Soc.  2008,  130:  6720 
    Google Scholar
  • 2e Lettan RB. Woodward CC. Scheidt KA. Angew. Chem. Int. Ed.  2008,  47:  2294 
    Google Scholar
  • 3a Brook AG. Duff JM. Joens PF. Davis NR.
    J. Am. Chem. Soc.  1967,  89:  431 
    Google Scholar
  • 3b Corey EJ. Seebach D. Freedman R. J. Am. Chem. Soc.  1967,  89:  434 
    Google Scholar
  • 4 Capperucci A. Degl’Innocenti A. Faggi C. Ricci A. J. Org. Chem.  1988,  53:  3612 
    Google Scholar
  • 5 Kondo J. Shinokubo H. Oshima K. Org. Lett.  2006,  8:  1185 
    Google Scholar
  • 6a Kondo J. Shinokubo H. Oshima K. Angew. Chem. Int. Ed.  2003,  42:  825 
    Google Scholar
  • 6b Onyeozili EN. Maleczka RE. Chem. Commun.  2006,  2466 
    Google Scholar
  • 7 Brook AG. Adv. Organomet. Chem.  1968,  7:  96 
    Google Scholar
  • 8 Buynak JD. Strickland JB. Hurd T. Phan A. J. Chem. Soc., Chem. Commun.  1989,  89 
    Google Scholar
  • 9a Paredes MD. Alonso R. J. Org. Chem.  2000,  65:  2292 
    Google Scholar
  • 9b Nicewicz DA. Yates CM. Johnson JS.
    J. Org. Chem.  2004,  69:  6548 
    Google Scholar
  • 10 Honda M. Ohkura N. Saisyo S.-I. Segi M. Nakajima T. Tetrahedron  2003,  59:  8203 
    Google Scholar
  • 11a Obora Y. Ogawa Y. Imai Y. Kawamura T. Tsuji Y. J. Am. Chem. Soc.  2001,  123:  10489 
    Google Scholar
  • 11b Linhu X. Johnson JS. Angew. Chem. Int. Ed.  2003,  42:  2534 
    Google Scholar
  • 11c Linhu X. Potnick JR. Johnson JS. J. Am. Chem. Soc.  2004,  126:  3070 
    Google Scholar
  • 11d Nahm MR. Linghu X. Potnick JR. Yates CM. White PS. Johnson JS. Angew. Chem. Int. Ed.  2005,  44:  2377 
    Google Scholar
  • 11e Nahm MR. Potnick JR. White PS. Johnson JS. J. Am. Chem. Soc.  2006,  128:  2751 
    Google Scholar
  • 11f Tarr JC. Johnson JS. Org. Lett.  2009,  11:  3870 
    Google Scholar
  • 11g Bower J. Box MB. Czyewski M. Goeta AE. Steel PG. Org. Lett.  2009,  11:  2744 
    Google Scholar
  • 11h Steward KM. Johnson JS. Org. Lett.  2010,  12:  2864 
    Google Scholar
  • 12a Mattson AE. Scheidt KA. Org. Lett.  2004,  6:  4363 
    Google Scholar
  • 12b Jonet S. Cherouvrier F. Brigaud T. Portella C. Eur. J. Org. Chem.  2005,  4304 
    Google Scholar
  • 12c Liu B. Lu CD. J. Org. Chem.  2011,  76:  4205 
    Google Scholar
  • 13 Garret MR. Tarr JC. Johnson JS. J. Am. Chem. Soc.  2007,  129:  12944 
    Google Scholar
  • 14a Takeda K. Nakajima A. Takeda M. Okamoto Y. Sato T. Yoshii E. Koizumi T. Shiro M. J. Am. Chem. Soc.  1998,  120:  4947 
    Google Scholar
  • 14b Nicewicz DA. Yates CM. Johnson JS. Angew. Chem. Int. Ed.  2004,  43:  2652 
    Google Scholar
  • 14c Shindo M. Matsumoto K. Shishido K. Chem. Commun.  2005,  2477 
    Google Scholar
  • 14d Shen Z. Dong VM. Angew. Chem. Int. Ed.  2009,  48:  784 
    Google Scholar
  • 14e Li FQ. Zhong S. Lu G. Chan ASC. Adv. Synth. Catal.  2009,  351:  1955 
    Google Scholar
  • 14f Lettan RB. Galliford CV. Woodward CC. Scheidt KA. J. Am. Chem. Soc.  2009,  131:  8805 
    Google Scholar
  • 14g Song Z. Kui L. Sun X. Li L. Org. Lett.  2011,  13:  1440 
    Google Scholar
  • 15 Sardina FJ. Rapoport H. Chem. Rev.  1996,  96:  1825 
    Google Scholar
  • 16a Ireland RE. Norbeck DW. J. Org. Chem.  1985,  50:  2198 
    Google Scholar
  • 16b Danheiser RL. Fink DM. Okano K. Tsai YM. Szczepanski SW. J. Org. Chem.  1985,  50:  5393 
    Google Scholar
  • 16c Patrocínio AF. Moran PJ. Synth. Commun.  1991,  31:  2457 
    Google Scholar
  • 16d Lipshutz BH. Lindsley C. Susfalk R. Gross T. Tetrahedron Lett.  1994,  35:  8999 
    Google Scholar
  • The synthesis of 4:
  • 17a Yang Y. Wang L. Fan R. J. Org. Chem.  2010,  75:  1760 
    Google Scholar
  • 17b Xu C. Bartley JK. Enache DI. Knignt DW. Hutchings GJ. Synthesis  2005,  3468 
    Google Scholar
  • 17c Wang JJ. Han GF. Wu XR. Yin JG. Zhao Y. Chin. J. Org. Chem.  2003,  23:  827 
    Google Scholar
  • 17d Wang GW. Lu QQ. Xia JJ. Eur. J. Org. Chem.  2011,  4429 
    Google Scholar
  • The preparation of 2-benzyl-3-hydroxy-5,5-dimethyl-cyclohex-2-enone and its analogues 3f and 3g were carried out according to previous reports:
  • 18a Lertpibulpanya D. Marsden SP. Org. Biomol. Chem.  2006,  4:  3498 
    Google Scholar
  • 18b Ramachary DB. Kishor M. J. Org. Chem.  2007,  72:  5056 
    Google Scholar
  • 18c Kennedy JWJ. Vietrich S. Weinmann H. Dominic EA. J. Org. Chem.  2008,  73:  5151 
    Google Scholar
  • 19a Wright A. West R. J. Am. Chem. Soc.  1974,  96:  3227 
    Google Scholar
  • 19b Biellmann JF. Ducep JB. Org. React.  1982,  27:  1 
    Google Scholar
  • 19c Hwu JR. Tsay SC. Wang N. Hakimelahi GH. Organometallics  1994,  13:  2461 
    Google Scholar
  • 19d Nelkenbaum E. Kapon M. Eisen MS. J. Organomet. Chem.  2005,  690:  2297 
    Google Scholar
  • 20a Allred AL. Rochow EG. J. Inorg. Nucl. Chem.  1958,  5:  264 
    Google Scholar
  • 20b Brook MA. Silicon in Organic, Organometallic, and Polymer Chemistry   Wiley-Interscience; New York: 1999. 
    Google Scholar
  • 20c Chen XH. Deng Y. Jiang K. Lai GQ. Ni Y. Yang KF. Jiang JX. Xu LW. Eur. J. Org. Chem.  2011,  1736 
    Google Scholar
  • 20d Xu LW. Li L. Lai GQ. Jiang JX. Chem. Soc. Rev.  2011,  40:  1777 ; and references cited therein
    Google Scholar
  • Selected reviews:
  • 21a Sheldon RA. Arends IWCE. Brink GJT. Dijksman AA. Acc. Chem. Res.  2002,  35:  774 
    Google Scholar
  • 21b Mallat T. Baiker A. Chem. Rev.  2004,  104:  3037 
    Google Scholar
  • 21c Schultz MJ. Sigman MS. Tetrahedron  2006,  62:  8227 
    Google Scholar
  • 21d Carbon S. Dugger RW. Ruggeri SG. Ragan JA. Ripin DHB. Chem. Rev.  2006,  106:  2943 
    Google Scholar
  • Selected recent examples:
  • 22a Han CY. Yu M. Sun WJ. Yao XQ. Synlett  2011,  2363 
    Google Scholar
  • 22b Tsukamoto D. Ikeda M. Shiraishi Y. Hara T. Ichikuni N. Tanaka S. Hirai T. Chem. Eur. J.  2011,  17:  9816 
    Google Scholar
  • 22c van der Toorn JC. Kemperman G. Sheldon RA. Arends IWCE. Eur. J. Org. Chem.  2011,  4345 
    Google Scholar
  • 22d Verma S. Nandi M. Modak A. Jain SL. Bhaumik A. Adv. Synth. Catal.  2011,  353:  1897 
    Google Scholar
  • 22e Simon MO. Ung G. Darses S. Adv. Synth. Catal.  2011,  353:  1045 
    Google Scholar
  • 22f Shibuya M. Osada Y. Sasano Y. Tomizawa M. Iwabuchi Y. J. Am. Chem. Soc.  2011,  133:  6497 
    Google Scholar
  • 22g Karimi B. Farhangi E. Chem. Eur. J.  2011,  17:  6056 
    Google Scholar
  • 22h Qi XY. Wang J. Zheng LW. Qi L. Synlett  2011,  555 
    Google Scholar
  • 22i Yuan Y. Shi XA. Liu W. Synlett  2011,  559 
    Google Scholar
  • 22j Wu S. Ma H. Lei ZQ. Synlett  2010,  2818 
    Google Scholar
  • Selected examples:
  • 23a Hoye TR. Feffrey CS. Tennakoon MA. Wang J. Zhao H. J. Am. Chem. Soc.  2004,  126:  10210 
    Google Scholar
  • 23b Smith AB. Duffey MO. Synlett  2004,  1363 
    Google Scholar
  • 23c Smith AB. Xian M. J. Am. Chem. Soc.  2006,  128:  66 
    Google Scholar
  • 23d Smith AB. Xian M. Kim WS. Kim DS. J. Am. Chem. Soc.  2006,  128:  12368 
    Google Scholar
  • 23e Smith AB. Kim DS. Xian M. Org. Lett.  2007,  9:  3307 
    Google Scholar
  • 23f Smith AB. Kim DS. Xian M. Org. Lett.  2007,  9:  3311 
    Google Scholar
  • 23g Smith AB. Kim DS. Wuest WM. Angew. Chem. Int. Ed.  2008,  47:  7082 
    Google Scholar
  • 23h Sorimachi K. Terada M. J. Am. Chem. Soc.  2008,  130:  14452 
    Google Scholar
  • 23i Han ZY. Xiao H. Chen XH. Gong LZ. J. Am. Chem. Soc.  2009,  131:  9182 
    Google Scholar
  • 23j Wang J. Zhou P. Wang Y. Eur. J. Org. Chem.  2011,  264 
    Google Scholar