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. 2019 Dec 26;18(1):24. doi: 10.3390/md18010024

Table 3.

Stille-based cross-coupling conditions with iodoenaminone 17.

graphic file with name marinedrugs-18-00024-i002.jpg

Entry Conditions R Result
1 CH2C(OZnBr)OtBu, Pd2(dba)3/dppf, THF CH2CO2tBu 18a (decomp.)
2 CH2C(OSnnBu3)OEt, PdCl2(P(o-tol)3)2, CuF2 CH2CO2Et 18b (N.R.)
3 nBu3SnCH=CH2, Pd(PPh3)4, CuI CH=CH2 18c (< 5%)
4 nBu3SnCH=CH(OEt), Pd(PPh3)4, CuCl, LiCl, THF CH=CH(OEt) 18d (67%)
5 nBu3SnCH=C(OEt)2, Pd(PPh3)4, CuCl, LiCl, THF CH=C(OEt)2 19 (0–40%)
6 nBu3SnCH=C(OEt)2, Pd(PPh3)4, CuTC, THF CH=C(OEt)2 19 (60%)

CuTC = Copper (I) thiophene-2-carboxylate.