Please do not adjust margins
Organic & Biomolecular Chemistry
Page 4 of 4
COMMUNICATION
Journal Name
DOI: 10.1039/C8OB00810H
Lee, RSC Adv., 2013, 3, 14165.
2. (a) W. Wang, H. Huang, C. Yu, X. Li, Y. Zhang, Y. Zhang, X.
Chen, P. S. Mariano and H. Xie, Angew. Chem., Int. Edit.,
2017, 56, 8201; (b) H. Huang, X. Li, C. Yu, Y. Zhang, P. S.
Mariano and W. Wang, Angew. Chem., Int. Edit., 2017, 129
,
1522; (c) H. Huang, C. Yu, Y. Zhang, Y. Zhang, P. S. Mariano
and W. Wang, J. Am. Chem. Soc., 2017, 139, 9799.
3. S. Zhang, Z. Tan, H. Zhang, J. Liu, W. Xu and K. Xu, Chem.
Commun., 2017, 53, 11642.
4. Y. Liu, L. Cai, S. Xu, W. Pu and X. Tao, Chem. Commun., 2018,
54, 2166.
5. D.-Z. Lin and J.-M. Huang, Org. Lett., 2018, 20, 2112-2115.
6. (a) G. E. Dobereiner and R. H. Crabtree, Chem. Rev., 2009,
Scheme 2. Proposed reaction pathway.
110, 681; (b) H. M. Davies, Angew. Chem., Int. Edit., 2006, 45
,
6422; (c) H. M. Davies, J. Du Bois and J.-Q. Yu, Chem. Soc.
Rev., 2011, 40, 1855; (d) P. B. Arockiam, C. Bruneau and P. H.
Dixneuf, Chem. Rev., 2012, 112, 5879; (e) X. Chen, K. M.
Engle, D. H. Wang and J. Q. Yu, Angew. Chem., Int. Edit.,
2009, 48, 5094; (f) C.-J. Li, Acc. Chem. Res., 2008, 42, 335.
7. (a) W. R. Gutekunst and P. S. Baran, Chem. Soc. Rev., 2011,
Based on the results of our control experiments, we
excluded the possibilities that involving 2-(1H-indol-3-yl)-2-
oxoacetic acid (Scheme 2, eq. 1; dehydrogenation prior to
decarboxylation) or formaldehyde (Scheme 2, eq. 2;
decarboxylation prior to dehydrogenation) as the reaction
intermediates. The dehdrogenative coupling step and
decarboxylative step may occur in a concurrent manner
(Scheme 2, eq. 3). In this system, copper might act as oxidant
to regenerate catalyst and silver re-oxidize copper. Iron helps
the activation of indole.
In summary, we have studied the dehdrogenative-
decarboxylative coupling of indoles with glyoxylic acid. This
transformation enables for the facile generation of various 3-
formylindoles in moderate to good yields with good functional
group tolerance. Notably, no N-formylation product was
detected under our conditions.
40, 1976; (b) R. J. Phipps and M. J. Gaunt, Science, 2009, 323
,
1593; (c) Z. Li, L. Cao and C. J. Li, Angew. Chem., Int. Edit.,
2007, 119, 6625; (d) H.-Q. Do, R. M. K. Khan and O. Daugulis,
J. Am. Chem. Soc., 2008, 130, 15185; (e) H.-Q. Do and O.
Daugulis, J. Am. Chem. Soc., 2008, 130, 1128.
8. M. Zhang, J. Zhou, J. Kan, M. Wang, W. Su and M. Hong,
Chem. Commun., 2010, 46, 5455.
9. (a) Z. Yin, Z. Wang and X. F. Wu, ChemistrySelect, 2017,
2
,
,
6689; (b) Z. Wang, Z. Yin and X.-F. Wu, Org. Lett., 2017, 19
4680; (c) Z. Wang, Z. Yin and X.-F. Wu, Chem. Commun.,
2018, DOI: 10.1039/c8cc01784k.
10. (a) H. Wang, L. N. Guo and X. H. Duan, Adv. Synth. Catal.,
2013, 355, 2222; (b) F. Hu, X. Shao, D. Zhu, L. Lu and Q. Shen,
Angew. Chem., Int. Edit., 2014, 53, 6105; (c) H. Kim and P. H.
Lee, Adv. Synth. Catal., 2009, 351, 2827; (d) X. Liu, Z. Wang,
X. Cheng and C. Li, J. Am. Chem. Soc., 2012, 134, 14330; (e) F.
Acknowledgements
The analytic supports of Dr. W. Baumann, Dr. C. Fisher, S.
Buchholz, and S. Schareina are gratefully acknowledged. We
also appreciate the general supports from Professors Matthias
Beller and Armin Börner in LIKAT.
Yin, Z. Wang, Z. Li and C. Li, J. Am. Chem. Soc., 2012, 134
10401.
,
11. Other substrates see supplemetary imformation.
References
1. (a) L. J. Gooßen, N. Rodriguez and K. Gooßen, Angew. Chem.,
Int. Edit., 2008, 47, 3100; (b) N. Rodriguez and L. J. Goossen,
Chem. Soc. Rev., 2011, 40, 5030; (c) J. D. Weaver, A. Recio III,
A. J. Grenning and J. A. Tunge, Chem. Rev., 2011, 111, 1846;
(d) Z. Li, Y. Y. Jiang, A. A. Yeagley, J. P. Bour, L. Liu, J. J.
Chruma and Y. Fu, Chem. Eur. J., 2012, 18, 14527; (e) H.-Q.
Luo, W. Dong and T.-P. Loh, Tetrahedron Lett., 2013, 54
,
2833; (f) A. J. Borah and G. Yan, Org. Biomol. Chem., 2015,
13, 8094; (g) C. Shen, P. Zhang, Q. Sun, S. Bai, T. A. Hor and X.
Liu, Chem. Soc. Rev., 2015, 44, 291; (h) M. O. Konev and E. R.
Jarvo, Angew. Chem., Int. Edit., 2016, 55, 11340; (i) Y. Wei, P.
Hu, M. Zhang and W. Su, Chem. Rev., 2017, 117, 8864; (j) R.
4 | J. Name., 2012, 00, 1-3
This journal is © The Royal Society of Chemistry 20xx
Please do not adjust margins