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. Author manuscript; available in PMC: 2013 Aug 29.
Published in final edited form as: J Am Chem Soc. 2012 Aug 20;134(34):14232–14237. doi: 10.1021/ja306323x

Table 1.

Palladium-Catalyzed Elimination of an Alkyl Bromide to Generate an Olefin: Influence of Reaction Parameters

graphic file with name nihms-402431-f0004.jpg
entry variation from the “standard” conditions yield (%)a
1 none 98 (91)
2 no Pd(P(t-Bu)2Me)2 3
3 no KOt-Bu 95 (81)
4 no Cy2NH 13
5 Pd(P(t-Bu)3)2, instead of Pd(P(t-Bu)2Me)2 3
6 Pd(PCy3)2, instead of Pd(P(t-Bu)2Me)2 12
7 Pd(PPh3)4, instead of Pd(P(t-Bu)2Me)2 3
8 Cy2NMe, instead of Cy2NH 42
9 Cs2CO3, instead of Cy2NH 28
10 3% Pd2(dba)3 + 12% P(t-Bu)2Me, instead of Pd(P(t-Bu)2Me)2 96 (76)
11 3%, instead of 6%, Pd(P(t-Bu)2Me)2 90 (75)
a

Determined via gas chromatography with the aid of a calibrated internal standard (average of two experiments); the yield after 4 h is given in parentheses.