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. Author manuscript; available in PMC: 2012 May 4.
Published in final edited form as: J Am Chem Soc. 2011 Apr 8;133(17):6541–6544. doi: 10.1021/ja2015586

Table 2.

Pd-Catalyzed Olefination and Cyclization Between Various Pyridines and Ethyl Acrylate.

Entry Substrate Product Yield
1 [a] graphic file with name nihms-287954-t0005.jpg graphic file with name nihms-287954-t0006.jpg 89%
2 [a] graphic file with name nihms-287954-t0007.jpg graphic file with name nihms-287954-t0008.jpg 81% (dr = 1.2 : 1)
3 [a] graphic file with name nihms-287954-t0009.jpg graphic file with name nihms-287954-t0010.jpg 55% (dr = 1.2 : 1)
4 [a] graphic file with name nihms-287954-t0011.jpg graphic file with name nihms-287954-t0012.jpg 43% (dr = 2.4 : 1)
5 [b] graphic file with name nihms-287954-t0013.jpg graphic file with name nihms-287954-t0014.jpg 70%
6 [b] graphic file with name nihms-287954-t0015.jpg graphic file with name nihms-287954-t0016.jpg 71%
7 [b] graphic file with name nihms-287954-t0017.jpg graphic file with name nihms-287954-t0018.jpg 75%
8 [b] graphic file with name nihms-287954-t0019.jpg graphic file with name nihms-287954-t0020.jpg 36%
9 [b] graphic file with name nihms-287954-t0021.jpg graphic file with name nihms-287954-t0022.jpg 49% (dr = 1 : 1)
10 [b] graphic file with name nihms-287954-t0023.jpg graphic file with name nihms-287954-t0024.jpg 39%
[a]

Conditions: 1.1 equiv of NaOTf, 10 mol % of Pd(MeCN)4(BF4)2, 3 mol % of H4[PMo11VO40], 5 equiv of ethyl acrylate, AcOH, air, 110 °C, 18 h.

[b]

Conditions: (i) 10 mol % of NaOAc, 10 mol % of Pd(MeCN)4(BF4)2, 3 mol % of H4[PMo11VO40], 5 equiv of ethyl acrylate , AcOH, air, 110 °C, 18 h; (ii) saturated aq. NaBF4.