Advanced Synthesis & Catalysis
10.1002/adsc.202000426
anhyd. Na
2
SO
4
and concentrated under reduced pressure.
Liu, Y. Niu, Y. -F. Wu, X. -S. Ye, Org. Lett. 2016, 18,
1836; d) A. Modak, T. Patra, R. Chowdhury, S. Raul, D.
Maiti, Organometallics, 2017, 36, 2418; e) C. He, M. J.
Gaunt, Chem. Sci. 2017, 8, 3586; f) G. -J. Cheng, Y. -F.
Yang, P. Li, P. Chen, T. -Y. Sun, G. Li, X. Zhang, K. N.
Houk, J. -Q. Yu, Y. -D. Wu, J. Am. Chem. Soc. 2014,
136, 894; g) B. ‐ F. Shi, N. Maugel, Y. ‐ H. Zhang, J.
‐ Q. Yu, Angew. Chem. Int. Ed. 2008, 47, 4882; h) P. S.
Thuy-Boun, G. Villa, D. Dang, P. Richardson, S. Su, J.
-Q. Yu, J. Am. Chem. Soc. 2013, 135, 17508; i) B. E.
Haines, D. G. Musaev, ACS Catal. 2015, 5, 830; j) W.
Yang, S. Ye, Y. Schmidt, D. Stamos, J. ‐ Q. Yu, Chem.
Eur. J. 2016, 22, 7059; k) B. E. Haines, J. -Q. Yu, D. G.
Musaev, ACS Catal. 2017, 7, 4344.
The crude products were adsorbed on silica gel and pass
through the column (eluent: Hexane/EtOAc) to get
analytically pure product 3a, white solid (32.4 mg, 84%);
1
mp: 84–85 ℃; H NMR (500 MHz CDCl
3
): δ 8.15 (s, 1H),
7
7
=
1
1
1
.95 (d, J = 8.0 Hz, 1H), 7.67 (dd, J = 8.0, 1.5 Hz,2H),
.44 (t, J = 7.7 Hz, 2H), 7.40 (d, J = 8.0 Hz, 1H), 7.33 (d, J
2.6 Hz, 1H), 7.30 – 7.23 (m, 2H), 7.19 (td, J = 7.4, 6.9,
.1 Hz, 1H); 1 C NMR (125 MHz CDCl
3
): δ 136.7, 135.6,
3
28.8, 127.5, 126.0, 125.8, 122.5, 121.8, 120.4, 119.9,
18.4, 111.4;HRMS (ESI-TOF) m/z: [M + H] Calcd for
+
14
C H11N 194.0964, Found 194.0961.
Representative tandem decarboxylation/C3-arylation of
indole: To dried tube equipped with a stir bar,
[
3] The utilized amino acid for the C-H functionalizations
usually protected, either C- or N-terminals.
[
2
(cinnamyl)PdCl] (5.2 mg, 0.01 mmol, 5 mol%), L-
Aspartic acid (2.7 mg, 0.02 mmol, 10 mol%), 1H-indole-3-
carboxylic acid 25 (32.2 mg, 0.2 mmol), bromobenzene 2a
[4] Recent review: a) F. R. De Sa Alves, E. J. Barreiro, C.
A. M. Fraga, Mini-Rev. Med. Chem. 2009, 9, 782; b) N.
K. Kaushik, N. Kaushik, P. Attri, N. Kumar, C. H. Kim,
A. K. Verma, E. H. Choi, Molecules, 2013, 18, 6620; c)
S. Emami, S. Dadashpour, Eur. J. Med. Chem. 2018,
150, 9; d) E. Ozcan, H. H. Kazan, B. Çoşut,
Luminescence 2019, 35, 1; e) Y. Li, J. Yang, L. Niu,
D. Hu, H. Li, L. Chen, Y. Yu, Q. Ch, FEBS Lett.
2020, 594, 199; f) A. Kumari, R. K. Singh, Bioorg.
Chem. 2019, 89, 103021.
(
31.1 µL, 47.1 mg, 0.3 mmol, 1.5 equiv), K
3 4
PO (84.9 mg,
0
.4 mmol, 2 equiv), and THF (1 mL) were added and the
resultant reaction mixture was stirred at 100 °C for 24 h.
The cooled (room temp.) reaction mixture was subject to
aq. workup and extracted with EtOAc. The collected
organic layers were dried over anhyd. Na SO and
2 4
concentrated under reduced pressure. The crude products
were adsorbed on silica gel and pass through the column
(
(
eluent: Hexane/EtOAc) to get analytically pure product 3a
23.9 mg, 62%).
[
5] a) K. J. Hock, A. Knorrscheidt, R. Hommelsheim, J.
Ho, M. J. Weissenborn, R. M. Koenigs, Angew. Chem.
Int. Ed. 2019, 58, 3630; b) U. Sharma, R. Kumar, I.
Kumar, Synthesis, 2018, 50, 2655; c) G. N. Vaidya, A.
Khan, S. Kumar, D. Kumar, J. Org. Chem. 2019, 84,
Acknowledgments
Authors thanks the Department of Pharmaceuticals (DoP),
Ministry of Chemical and Fertilizers, and NIPER-Ahmedabad for
financial support. DK hearty acknowledge Prof. Kiran Kalia,
Director NIPER-A for her constant support, encouragement, and
motivation. DK also gratefully acknowledges the DST-SERB for
the award of Ramanujan Fellowship (File No. SB/S2/RJN-
3
004; d) J. A. Leitch, Y. Bhonoah, C. G. Frost, ACS
Catal. 2017, 7, 5618; e) D. Ma, Q. Cai, Synlett, 2004,
1
4
28; f) J. Liu, J. Yan, D. Qin, Q. Cai, Synthesis, 2014,
6, 1917; g) N. K. Mishra, M. Choi, H. Jo, Y. Oh, S.
Sharma, S. H. Han, T. Jeong, S. Han, S. -Y. Lee, I. S.
Kim, Chem. Commun. 2015, 51, 17229.
1
35/2017).
[
6]a) M. Yamaguchi, K. Suzuki, Y. Sato, K. Manabe, Org.
Lett. 2017, 19, 5388; b) T. Bzeih, D. Lamaa, G. Frison,
A. Hachem, N. Jaber, J. Bignon, P. Retailleau, M.
Alami, A. Hamze, Org. Lett. 2017, 19, 6700; c) S.
Vásquez-Céspedes, K. M. Chepiga, N. Möller, A. H.
Schäfer, F. Glorius, ACS Catal. 2016, 6, 5954; d) S. G.
Modha, M. F. Greaney, J. Am. Chem. Soc. 2015, 137,
References
[
1] a) K. M. Engle, Pure Appl. Chem. 2016, 88, 119; b) D.
G. Musaev, T. M. Figg, A. L. Kaledin, Chem. Soc. Rev.
2
014, 43, 5009; c) K. M. Engle, J. -Q. Yu, J. Org.
Chem. 2013, 78, 8927; d) B. Niu, K. Yang, B.
Lawrence, H. Ge, ChemSusChem 2019, 12, 2955; e) J.
J. Gair, B.E. Haines, A. S. Filatov, D. G. Musaev, J. C.
Lewis, ChemRxiv 2019, 1; f) W. Liu, J. Zheng, Z. Liu,
W. Hu, X. Wang and Y. Dang, ACS Catal. 2018, 8,
1
416; e) S. Chen, Y. Liao, F. Zhao, H. H. Qi, S. Liu, G.
Deng, J. Org. Lett. 2014, 16, 1618; f) Y. Chen, S. Guo,
K. Li, J. Qu, H. Yuan, Q. Hua, B. Chen, Adv. Synth.
Catal. 2013, 355, 711; g) Y. Huang, T. Ma, P. Huang,
D. Wu, Z. Lin, R. Cao, ChemCatChem, 2013, 5, 1877;
h) C. Y. He, S. Fan, X. Zhang, J. Am. Chem. Soc. 2010,
7
3
698; g) T. G. Appleton, Coord. Chem. Rev. 1997, 166,
13; h) R.-Y. Zhu, T. G. Saint-Denis, Y. Shao, J. He, J.
D. Sieber, C. H. Senanayake, J.-Q. Yu, J. Am. Chem.
Soc. 2017, 139, 5724; i) K. K. Pasunooti, B. Banerjee,
T. Yap, Y. Jiang, C.-F. Liu, Org. Lett. 2015, 17, 6094;
j) Y. Park, Z. L. Niemeyer, J.-Q. Yu, M. S. Sigman,
Organometallics 2018, 372, 203.
1
32, 12850; i) L. Joucla, N. Batail, L. Djakovitch, Adv.
Synth. Catal. 2010, 352, 2929; j) L. Ackermann, S.
Barfüßer, Synlett 2009, 808; k) B. Join, T. Yamamoto,
K. Itami, Angew. Chem. Int. Ed. 2009, 48, 3644; l) R. J.
Phipps, N. P. Grimster, M. J. Gaunt, J. Am. Chem. Soc.
2
2
008, 130, 8172; m) D. R. Stuart, K. Fagnou, Science,
007, 316, 1172; n) T. A. Dwight, N. R. Rue, D.
[
2] a) Y. -J. Liu, Z. -X. Zhou, D. Xie, X. -P. Luo, H. Wang,
B. Liu, M. -H. Zeng, Org. Lett. 2018, 20, 7274; b) R. E.
Plata, D. E. Hill, B. E. Haines, D. G. Musaev, L. Chu,
D. P. Hickey, M. S. Sigman, J. -Q. Yu, D. G.
Blackmond, J. Am. Chem. Soc. 2017, 139, 9238; c) M.
Charyk, R. Josselyn, B. DeBoef, Org. Lett. 2007, 9,
137; o) D. R. Stuart, E. Villemure, K. Fagnou, J. Am.
3
Chem. Soc. 2007, 129, 12072; p) B. S. Lane, M. A.
6
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