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. Author manuscript; available in PMC: 2014 Sep 5.
Published in final edited form as: Chem Rev. 2013 Jun 17;113(8):5701–5765. doi: 10.1021/cr4000144

Table 19.

Cross-coupling Reactions of Bridged Sultams by Paquette and Evans

graphic file with name nihms495222t21.jpg
entry conditions R 548 yield
(%)
1 MeLi/Me2SO4 -CH3 548a 70
2 MeLi/BrCH2Ph -CH2Ph 548b 58
3 tBuLi/ClCOtBu -C(O)tBu 548c 44
4 tBuLi/ClCOOBn -C(O)OBn 548d 33
5 MeLi/TMSCl -SiMe3 548e 40
6 tBuLi/Bu3SnCl -SnBu3 548f 57
7 tBuLi/PhSeCl -SePh 548g 55
8 Pd(PPh3)4, CuI, HC≡CC4H9 -C≡CC4H9 548h 10
9 PPh3, Pd(OAc)2
Cs2CO3, ArB(OH)2 		C6H5 548i 63
10 as above 2-MeO-C6H4 548j 76
11 as above 4-MeO-C6H4 548k 84
12 as above 2-Naphthyl 548l 84