Skip to main content
. Author manuscript; available in PMC: 2012 Nov 9.
Published in final edited form as: J Am Chem Soc. 2011 Oct 18;133(44):17630–17633. doi: 10.1021/ja208572v

Table 1.

Screening of Reaction Conditions for C–O Cyclization

graphic file with name nihms-332940-f0009.jpg
entry Pd-cat. oxidant solvent yield, %a
2a 2a’
1b Pd(OPiv)2 PhI(OAc)2 (1.5 eq) PhMe 43 (74) 2
2 Pd(OPiv)2 PhI(OAc)2 (1.5 eq) PhMe 50 (65) 3
3 Pd(OAc)2 PhI(OAc)2 (1.5 eq) PhMe 40 (67) 3
4 Pd(OTf)2 PhI(OAc)2 (1.5 eq) PhMe 40 (78) 2
5 Pd(OPiv)2 PhI(OAc)2 (1.5 eq) C6F6 37 (45) 3
6 Pd(OPiv)2 PhI(OAc)2 (1.5 eq) PhCF3 47 (53) 14
7 Pd(OPiv)2 PhI(OAc)2 (2.0 eq) PhMe 58 (79) 6
8 Pd(OPiv)2 PhI(OAc)2 (3.0 eq) PhMe 47 (52) 6
9 none PhI(OAc)2 (1.5 eq) PhMe 0 0
a

GC yields against tetradecane as internal standard, brsm yields in the parentheses (based on recovered starting material).

b

Li2CO3 (1 equiv) was added.