欢迎登录材料期刊网

材料期刊网

中国科学院金属研究所 科学出版社
高级检索
  1. 首页
  2. 期刊
  3. 催化学报
  4. 三价铑催化苯甲酰胺与醌的C-H活化偶联

催化学报 , 2015, (1): 48-56. doi: 10.1016/S1872-2067(14)60245-X

三价铑催化苯甲酰胺与醌的C-H活化偶联

戚自松 1, , 李兴伟 2,

1.中国科学院大连化学物理研究所,辽宁大连,116023

2.中国科学院大连化学物理研究所,辽宁大连,116023

基金项目:   the Dalian Institute of Chemical Physics, Chinese Academy of Sciences and the National Natural Science Foundation of China (21272231).基金来源:中国科学院大连化学物理研究所   国家自然科学基金(21272231)  

关键词： 三价铑 , 碳氢活化 , 苯甲酰胺 , 芳基醌

Rh(III)-catalyzed C-H activation of benzamides:Coupling with quinones

Keywords： Rhodium(III) , C-H activation , Benzamides , Arylquinones

三价铑在氧化条件下催化N-烷基苯甲酰胺与醌反应生成芳基醌。在氧化还原中性条件下，经过偶联和内酯化反应可以得到2-羟基-6H-苯并[c]吡喃-6-酮。

Rh(III)‐catalyzed C–H activation of N‐(alkyl)benzamides in the oxidative coupling with various quinones. In addition, under redox‐neutral conditions, 2‐hydroxy‐6H‐benzo[c]chromen‐6‐ones were also obtained via a cascade of cross‐coupling followed by lactonization.

参考文献

[1] Gutekunst W R, Baran P S. Chem Soc Rev, 2011, 40:1976,2011.
[2] Yamaguchi J, Yamaguchi A D, Itami K. Angew Chem Int Ed, 2012, 51:8960,2012.
[3] McMurray L, O'Hara F, Gaunt M J. Chem Soc Rev, 2011, 40:1885,2011.
[4] Daugulis O, Do H Q, Shabashov D. Acc Chem Res, 2009, 42:1074,2009.
[5] Ackermann L, Vicente R, Kapdi A R. Angew Chem Int Ed, 2009, 48:9792,2009.
[6] Lyons T W, Sanford M S. Chem Rev, 2010, 110:1147,2010.
[7] Colby D A, Bergman R G, Ellman J A. Chem Rev, 2010, 110:624,2010.
[8] Ackermann L. Chem Rev, 2011, 111:1315,2011.
[9] Wencel-Delord J, Droge T, Liu F, Glorius F. Chem Soc Rev, 2011, 40:4740,2011.
[10] Yeung C S, Dong V M. Chem Rev, 2011, 111:1215,2011.
[11] Cho S H, Kim J Y, Kwak J, Chang S. Chem Soc Rev, 2011, 40:5068,2011.
[12] Wendlandt A E, Suess A M, Stahl S S. Angew Chem Int Ed, 2011, 50:11062,2011.
[13] Kuhl N, Hopkinson M N, Wencel-Delord J, Glorius F. Angew Chem Int Ed, 2012, 51:10236,2012.
[14] Wu X F, Neumann H, Beller M. Chem Rev, 2012, 113:1,2012.
[15] Engle K M, Mei T S, Wasa M, Yu J Q. Acc Chem Res, 2012, 45:788,2012.
[16] Li D D, He C L, Cai H T, Wang G W. Chin J Org Chem(李丹丹, 何程林, 蔡海婷, 王官武. 有机化学), 2013, 33:203,2013.
[17] Yan G B, Wu X M, Yang M H. Org Biomol Chem, 2013, 11:5558,2013.
[18] Ackermann L. Acc Chem Res, 2014, 47:281,2014.
[19] Zhang M, Zhang Y F, Jie X M, Zhao H Q, Li G, Su W P. Org Chem Front, 2014, 1:843,2014.
[20] Colby D A, Tsai A S, Bergman R G, Ellman J A. Acc Chem Res, 2011, 45:814,2011.
[21] Song G Y, Wang F, Li X W. Chem Soc Rev, 2012, 41:3651,2012.
[22] Kuhl N, Schröder N, Glorius F. Adv Synth Catal, 2014, 356:1443,2014.
[23] Rakshit S, Grohmann C, Besset T, Glorius F. J Am Chem Soc, 2011, 133:2350,2011.
[24] Huang X L, Huang J S, Du C L, Zhang X Y, Song F J, You J S. Angew Chem Int Ed, 2013, 52:12970,2013.
[25] Liu B Q, Fan Y, Gao Y, Sun C, Xu C, Zhu J. J Am Chem Soc, 2013, 135:468,2013.
[26] Neely J M, Rovis T. J Am Chem Soc, 2013, 135:66,2013.
[27] Shen Y Y, Liu G X, Zhou Z, Lu X Y. Org Lett, 2013, 15:3366,2013.
[28] Unoh Y, Hashimoto Y, Takeda D, Hirano K, Satoh T, Miura M. Org Lett, 2013, 15:3258,2013.
[29] Zhang X S, Zhu Q L, Zhang Y F, Li Y B, Shi Z J. Chem Eur J, 2013, 19:11898,2013.
[30] Dong Y, Liu G. Chem Commun, 2013, 49:8066,2013.
[31] Li B, Ma J F, Xie W J, Song H B, Xu S S, Wang B Q. Chem Eur J, 2013, 19:11863,2013.
[32] Zhao P, Wang F, Han K L, Li X W. Org Lett, 2012, 14:3400,2012.
[33] Zhao P, Niu R, Wang F, Han K L, Li X W. Org Lett, 2012, 14:4166,2012.
[34] Zhang T, Wu L M, Li X W. Org Lett, 2013, 15:6294,2013.
[35] Wang F, Song G Y, Du Z Y, Li X W. J Org Chem, 2011, 76:2926,2011.
[36] Wang F, Song G Y, Li X W. Org Lett, 2010, 12:5430,2010.
[37] Umeda N, Hirano K, Satoh T, Miura M. J Org Chem, 2009, 74:7094,2009.
[38] Guimond N, Gouliaras C, Fagnou K. J Am Chem Soc, 2010, 132:6908,2010.
[39] Du Y, Hyster T K, Rovis T. Chem Commun, 2011, 47:12074,2011.
[40] Hesp K D, Bergman R G, Ellman J A. J Am Chem Soc, 2011, 133:11430,2011.
[41] Li Y, Li B J, Wang W H, Huang W P, Zhang X S, Chen K, Shi Z J. An-gew Chem Int Ed, 2011, 50:2115,2011.
[42] Tsai A S, Tauchert M E, Bergman R G, Ellman J A. J Am Chem Soc, 2011, 133:1248,2011.
[43] Zhu C, Xie W Q, Falck J R. Chem Eur J, 2011, 17:12591,2011.
[44] Chan W W, Lo S F, Zhou Z Y, Yu W Y. J Am Chem Soc, 2012, 134:13565,2012.
[45] Karthikeyan J, Haridharan R, Cheng C H. Angew Chem Int Ed, 2012, 51:12343,2012.
[46] Kim J Y, Park S H, Ryu J, Cho S H, Kim S H, Chang S. J Am Chem Soc, 2012, 134:9110,2012.
[47] Schröder N, Wencel-Delord J, Glorius F. J Am Chem Soc, 2012, 134:8298,2012.
[48] Wencel-Delord J, Nimphius C, Wang H G, Glorius F. Angew ChemInt Ed, 2012, 51:13001,2012.
[49] Cui S L, Zhang Y, Wu Q F. Chem Sci, 2013, 4:3421,2013.
[50] Gong T J, Xiao B, Cheng W M, Su W, Xu J, Liu Z J, Liu L, Fu Y. J Am Chem Soc, 2013, 135:10630,2013.
[51] Hyster T K, Ruhl K E, Rovis T. J Am Chem Soc, 2013, 135:5364,2013.
[52] Li X W, Yu S J, Wang F, Wan B S, Yu X Z. Angew Chem Int Ed, 2013, 52:2577,2013.
[53] Zhen W C, Du Z Y, Li X W. Chin J Catal(甄文萃, 杜正银, 李兴伟. 催化学报), 2013, 34:679,2013.
[54] Lian Y J, Hummel J R, Bergman R G, Ellman J A. J Am Chem Soc, 2013, 135:12548,2013.
[55] Qi Z S, Li X W. Angew Chem Int Ed, 2013, 52:8995,2013.
[56] Xie F, Qi Z S, Li X W. Angew Chem Int Ed, 2013, 52:11862,2013.
[57] Zeng R, Wu S Z, Fu C L, Ma S M. J Am Chem Soc, 2013, 135:18284,2013.
[58] Samanta R, Narayan R, Antonchick A P. Org Lett, 2012, 14:6108,2012.
[59] Wang F, Song G Y, Du Z Y, Li X W. J Org Chem, 2011, 76:2926,2011.
[60] Yang L, Correia C A, Li C J. Org Biomol Chem, 2011, 9:7176,2011.
[61] Yang L, Qian B, Huang H M. Chem Eur J, 2012, 18:9511,2012.
[62] Zhu C, Falck J R. Chem Commun, 2012, 48:1674,2012.
[63] Zhang X Y, Wang F, Qi Z S, Yu S J, Li X W. Org Lett, 2014, 16:1586,2014.
[64] Gould S J. Chem Rev, 1997, 97:2499,1997.
[65] Marco-Contelles J, Molina M T. Curr Org Chem, 2003, 7:1433,2003.
[66] Liu J K. Chem Rev, 2006, 106:2209,2006.
[67] Zhang B, Salituro G, Szalkowski D, Li Z H, Zhang Y, Royo I, Vilella D, Dı́ez M T, Pelaez F, Ruby C, Kendall R L, Mao X Z, Griffin P, Calaycay J, Zierath J R, Heck J V, Smith R G, Moller D E. Science, 1999, 284:974,1999.
[68] Koyama J. Recent Pat Anti-Infect Drug Discovery, 2006, 1:113,2006.
[69] Verma R P. Anti-Cancer Agents Med Chem, 2006, 6:489,2006.
[70] Babula P, Adam V, Havel L, Kizek R. Ceska Slovens Farm, 2007, 56:114,2007.
[71] Ferreira I C F R, Vaz J A, Vasconcelos M H, Martins A. Anti-Cancer Agents Med Chem, 2010, 10:424,2010.
[72] Dandawate P R, Vyas A C, Padhye S B, Singh M W, Baruah J B. Mini-Rev Med Chem, 2010, 10:436,2010.
[73] Nowicka B, Kruk J. Biochim Biophys Acta, 2010, 1797:1587,2010.
[74] Cramer W A, Crofts A R. In:Photosynthesis. Vol. 1. New York:Academic Press, 1982. 387-467,1982.
[75] Bechtold T. In:Bechtold T, Mussak R, Eds. Handbook of Natural Colorants. New York:Wiley, 2009. 151-182,2009.
[76] Lin A J, Sartorelli A C. J Med Chem, 1976, 19:1336,1976.
[77] Fujiwara Y, Domingo V, Seiple I B, Gianatassio R, Del Bel M, Baran P S. J Am Chem Soc, 2011, 133:3292,2011.
[78] Wang J, Wang S, Wang G, Zhang J, Yu X Q. Chem commun, 2012, 48:11769,2012.
[79] Deb A, Manna S, Maji A, Dutta U, Maiti D. Eur J Org Chem, 2013, 2013:5251,2013.
[80] Echavarren A M, de Frutos Ó, Tamayo N, Noheda P, Calle P. J Org Chem, 1997, 62:4524,1997.
[81] Tamayo N, Echavarren A M, Paredes M C. J Org Chem, 1991, 56:6488,1991.
[82] Liebeskind L S, Riesinger S W. J Org Chem, 1993, 58:408,1993.
[83] Gan X W, Jiang W, Wang W, Hu L H. Org Lett, 2009, 11:589,2009.
[84] Itahara T. J Org Chem, 1985, 50:5546,1985.
[85] Engler T A, Reddy J P. J Org Chem, 1991, 56:6491,1991.
[86] Molina M T, Navarro C, Moreno A, Csákÿ A G. Org Lett, 2009, 11:4938,2009.
[87] Demchuk O M, Pietrusiewicz K M. Syntlett, 2009:1149,2009.
[88] Zhang S, Song F J, Zhao D B, You J S. Chem Commun, 2013, 49:4558,2013.
[89] de Oliveira R A, Carazza F, da Silva Pereira M O. Synth Commun, 2000, 30:4563,2000.
[90] Yoshida K, Oga N, Kadota M, Ogasahara Y, Kubo Y. J Chem Soc, Chem Commun, 1992:1114,1992.
[91] Engelman K L, Feng Y, Ison E A. Organometallics, 2011, 30:4572,2011.
[92] Zeng R, Fu C L, Ma S M. J Am Chem Soc, 2012, 134:9597,2012.
[93] Wang F, Qi Z S, Sun J Q, Zhang X L, Li X W. Org Lett, 2013, 15:6290,2013.
[94] Yang W, Sun J Q, Xu X X, Zhang Q, Liu Q. Chem Commun, 2014, 50:4420,2014.
[95] Ryu J, Shin K, Park S H, Kim J Y, Chang S. Angew Chem Int Ed, 2012, 51:9904,2012.
上一张 下一张
上一张 下一张
计量
  • 下载量()
  • 访问量()
作者相关
文章评分
  • 您的评分：
  • 1
    0%
  • 2
    0%
  • 3
    0%
  • 4
    0%
  • 5
    0%

版权所有©2010中国科学院金属研究所中国科技出版传媒股份有限公司

本系统由北京仁和汇智信息技术有限公司设计开发

技术支持：info@rhhz.net