期刊文献+

Rhodium(Ⅲ)-catalyzed [3+2] annulative coupling between oximes and electron-deficient alkynes

Rhodium(Ⅲ)-catalyzed [3+2] annulative coupling between oximes and electron-deficient alkynes
原文传递
导出
摘要 Rhodium(III)-catalyzed coupling between ketoximes and alkynes via C–H activation and annulation typically followed the[4+2]selectivity to afford isoquinolines.By designing alkynes bearing a highly electron-withdrawing group and under substrate control,we have successfully switched the selectivity of the coupling between oximes and alkynes to the alternative[3+2]annulation,leading to the efficient synthesis of indenamines.This process features good regioselectivity for both substrates,high efficiency,broad substrate scope,and excellent functional group tolerance. Rhodium(III)-catalyzed coupling between ketoximes and alkynes via C-H activation and annulation typically followed the [4+2] selectivity to afford isoquinolines. By designing alkynes bearing a highly electron-withdrawing group and under sub- strate control, we have successfully switched the selectivity of the coupling between oximes and alkynes to the alternative [3+2] annulation, leading to the efficient synthesis of indenamines. This process features good regioselectivity for both sub- strates, high efficiency, broad substrate scope, and excellent functional group tolerance.
出处 《Science China Chemistry》 SCIE EI CAS CSCD 2015年第8期1297-1301,共5页 中国科学(化学英文版)
基金 supported by the Dalian Institute of Chemical Physics,Chinese Academy of Sciences the National Natural Science Foundation of China(21472186,21272231)
关键词 rhodium(III) C-H activation ANNULATION OXIME ALKYNE 吸电子基团 耦合方法 III 催化 炔烃 C-H键
  • 相关文献

参考文献47

  • 1Bohme TM, Keim C, Kreutzmann K, Linder M, Dingermann T, Dannhardt G, Mutschler E, Lambrecht G. Structure-activity relationships of dimethindene derivatives as new M2-selective muscarinic receptor antagonists. J Med Chem, 2003, 46: 856-867.
  • 2a) Cheng YJ, Hsieh CH, He Y, Hsu CS, Li Y. Combination of indene-C60 bis-adduct and cross-linked fullerene interlayer leading to highly efficient inverted polymer solar cells. J Am Chem Soc, 2010, 132: 17381-17383.
  • 3He Y, Chen HY, Hou J, Li Y. Indene-C60 bisadduct: a new acceptor for high-performance polymer solar cells. J Am Chem Soc, 2010, 132: 1377-1382.
  • 4Zhao G, He Y, Li Y. 6.5% Efficiency of polymer solar cells based on poly(3-hexylthiophene) and indene-C60 bisadduct by device optimization. Adv Mater, 2010, 22: 4355-4358.
  • 5O’Brien X, Parker J, Lessard P, Sinskey A. Engineering an indene bioconversion process for the production of c/v-aminoindanol: a model system for the production of chiral synthons. Appl Microbiol Biotechnol, 2002, 59: 389-399.
  • 6a) Ackermann L, Vicente R, Kapdi AR. Transition-metal-catalyzed direct arylation of (hetero)arenes by C-H bond cleavage. Angew Chem Int Ed, 2009, 48: 9792-9826.
  • 7Arockiam PB, Bruneau C, Dixneuf PH. Ruthenium(II)-catalyzed C-H bond activation and functionalization. Chem Rev, 2012, 112: 5879-5918.
  • 8Chen X, Engle KM, Wang DH, Yu JQ. Palladium(II)-catalyzed C-H activation/C-C cross-coupling reactions: versatility and practicality. Angew Chem Int Ed, 2009, 48 : 5094—5115.
  • 9Cho SH, Kim JY, Kwak J, Chang S. Recent advances in the transition metal-catalyzed twofold oxidative C-H bond activation strategy for C-C and C-N bond formation. Chem Soc Rev, 2011, 40: 5068-5083.
  • 10Engle KM, Mei TS, Wasa M, Yu JQ. Weak coordination as a powerful means for developing broadly useful C-H functionalization reactions. AccChem Res, 2011, 45: 788-802.

相关作者

内容加载中请稍等...

相关机构

内容加载中请稍等...

相关主题

内容加载中请稍等...

浏览历史

内容加载中请稍等...
;
使用帮助 返回顶部