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. Author manuscript; available in PMC: 2013 Jul 9.
Published in final edited form as: Chemistry. 2011 May 26;17(28):7890–7903. doi: 10.1002/chem.201003489

Table 2.

Selected optimization studies for Pd-π-allyl alkylation of 22.

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Entry Substrate Pd Sourcea Solvent Ligand Yieldc
1 22a Pd2dba3·CHCl3 THF PPh3 23%
2 22a Pd2dba3·CHCl3 THF dppp 51%
3 22a Pd2dba3·CHCl3 THF P(OPh)3 67%
4 22a [{Pd(C3H5)Cl}2] THF P(OPh)3 69%
5 22a Pd2dba3·CHCl3 THF -- 23%
6 22b Pd2dba3·CHCl3 THF P(OPh)3 73%
7 22b Pd2dba3·CHCl3 DMSO P(OPh)3 75%
8 22b Pd2dba3·CHCl3 PhH P(OPh)3 23%
9 22b Pd2dba3·CHCl3 THF P(O-iPr)3 41%
10 22b Pd(OAc)2b THF P(OPh)3 86%
11 22b Pd(OAc)2 DMSO dppf 85%
12 22b Pd(dppe)2b DMSO -- 82%
a

10% of Pd source unless stated otherwise.

b

20% of Pd source.

c

All yields are isolated yields after silica gel chromatography.