A Catalyzed Aerobic Intramolecular C–O Bond Formation: Facile Access to Ring-Fused Dihydrobenzoxazine Derivatives

Published as part of the Special Topic Modern Strategies for Heterocycles Synthesis

Abstract

A catalyst comprising of catalytic cobalt(II) acetate/copper(II) acetate/dl-tyrosine with oxygen as the oxidant allows aerobic intramolecular C–O bond construction in [2-(pyrrolidin-1-yl)phenyl]methanol by free-radical promoted intramolecular selective functionalization of an (sp³)C–H bond by the alcohol, thus providing an environmentally friendly approach to 5H-benzo[d]pyrrolo[2,1-b][1,3]oxazine derivatives.

Key words

free radicals - C–H functionalization - cross-dehydrogenative coupling - aerobic oxidation - heterocycles

• References


For selected recent reviews on CDC reactions, see:
• 1a Li C.-J. Acc. Chem. Res. 2009; 42: 335
• 1b Yeung CS. Dong VM. Chem. Rev. 2011; 111: 1215
• 1c Girard SA. Knauber T. Li C.-J. Angew. Chem. Int. Ed. 2014; 53: 74
• 1d Jia F. Li Z. Org. Chem. Front. 2014; 1: 194
• 1e Guo X. Li Z. Li C. Prog. Chem. 2010; 22: 1434

For reviews on selective functionalization of sp³-α-C–H bond in simple aliphatic alcohols, see:
• 2a Zhang S. Zhang F. Tu Y.-Q. Chem. Soc. Rev. 2011; 40: 1937
• 2b Shang X. Liu Z.-Q. Huaxue Xuebao 2015; 73: 1275

For selected reviews on (sp³)C–H functionalization, see:
• 2c Bergman RG. Nature (London) 2007; 446: 391
• 2d Liu C. Zhang H. Shi W. Lei A. Chem. Rev. 2011; 111: 1780
• 2e Davies HM. L. Morton D. Chem. Soc. Rev. 2011; 40: 1857
• 2f Newhouse T. Baran PS. Angew. Chem. Int. Ed. 2011; 50: 3362
• 2g Engle KM. Mei T.-S. Wasa M. Yu J.-Q. Acc. Chem. Res. 2012; 45: 788
• 2h Roizen JL. Harvey ME. Du Bois J. Acc. Chem. Res. 2012; 45: 911
• 2i White MC. Science (Washington, D. C.) 2012; 335: 807
• 2j Rouquet G. Chatani N. Angew. Chem. Int. Ed. 2013; 52: 11726
• 2k Hartwig JF. J. Am. Chem. Soc. 2016; 138: 2
• 2l He J. Wasa M. Chan KS. L. Shao Q. Yu J.-Q. Chem. Rev. 2017;

For selected recent reviews on general C–H functionalization, see:
• 3a Le Bras J. Muzart J. Chem. Rev. 2011; 111: 1170
• 3b Sun C.-L. Li B.-J. Shi Z.-J. Chem. Rev. 2011; 111: 1293
• 3c Cho SH. Kim JY. Kwak J. Chang S. Chem. Soc. Rev. 2011; 40: 5068
• 3d Yamaguchi J. Yamaguchi AD. Itami K. Angew. Chem. Int. Ed. 2012; 51: 8960
• 3e Zhang C. Tang C. Jiao N. Chem. Soc. Rev. 2012; 41: 3464
• 3f Shang X. Liu Z.-Q. Chem. Soc. Rev. 2013; 42: 3253
• 3g Liu C. Yuan J. Gao M. Tang S. Li W. Shi R. Lei A. Chem. Rev. 2015; 115: 12138
• 3h Yang L. Huang H. Chem. Rev. 2015; 115: 3468
• 3i Guo X.-X. Gu D.-W. Wu Z. Zhang W. Chem. Rev. 2015; 115: 1622
• 3j Zheng Q.-Z. Jiao N. Chem. Soc. Rev. 2016; 45: 4590
• 3k Qin Y. Zhu L. Luo S. Chem. Rev. 2017;

For selected recent examples, see:
• 3l Huo C. Yuan Y. Wu M. Jia X. Wang X. Chen F. Tang J. Angew. Chem. Int. Ed. 2014; 53: 13544
• 3m Huo C. Tang J. Xie H. Wang Y. Dong J. Org. Lett. 2016; 18: 1016
• 3n Huo C. Dong J. Su Y. Tang J. Chen F. Chem. Commun. 2016; 52: 13341
• 4a Li Z. Zhang Y. Zhang L. Liu Z.-Q. Org. Lett. 2014; 16: 382
• 4b Li Z. Xiao Y. Liu Z.-Q. Chem. Commun. 2015; 51: 9969
• 4c Shang X.-J. Liu Z.-Q. Tetrahedron Lett. 2015; 56: 482
• 4d Liu Z.-Q. Li Z. Chem. Commun. 2016; 52: 14278
• 5a Liu Z.-Q. Sun L. Wang J. Han J. Zhao Y. Zhou B. Org. Lett. 2009; 11: 1437
• 5b Liu Z.-Q. Zhang Y. Zhao L. Li Z. Wang J. Li H. Wu L.-M. Org. Lett. 2011; 13: 2208
• 5c Cui Z. Shang X. Shao X.-F. Liu Z.-Q. Chem. Sci. 2012; 3: 2853
• 5d Li Z. Fan F. Yang J. Liu Z.-Q. Org. Lett. 2014; 16: 3396
• 5e Xu Z. Hang Z. Chai L. Liu Z.-Q. Org. Lett. 2016; 18: 4662
• 5f Xu Z. Hang Z. Liu Z.-Q. Org. Lett. 2016; 18: 4470

For selected reviews on catalyzed aerobic oxidation, see:
• 6a Stahl SS. Angew. Chem. Int. Ed. 2004; 43: 3400
• 6b Punniyamurthy T. Velusamy S. Iqbal J. Chem. Rev. 2005; 105: 2329
• 6c Piera J. Bäckvall J.-E. Angew. Chem. Int. Ed. 2008; 47: 3506
• 6d Shi Z. Zhang C. Tang C. Jiao N. Chem. Soc. Rev. 2012; 41: 3381
• 7 Carreira EM. Fessard TC. Chem. Rev. 2014; 114: 8257
• 8 Kienzle F. Tetrahedron Lett. 1983; 24: 2213