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. Author manuscript; available in PMC: 2017 Oct 1.
Published in final edited form as: Org Chem Front. 2016 Aug 22;3(10):1314–1318. doi: 10.1039/C6QO00215C

Table 3.

Comparison of Conditions for Chroman Synthesisa

graphic file with name nihms-812158-f0007.jpg
Entry R X Yieldb
1 H OTf 68
2 H Br 76c
3 OMe OTf 41
4 OMe Br 57c
5 C(O)Ph OTf 78
6 C(O)Ph Br 51c
a

Reaction Conditions for X = OTf: 1.0 equiv 1, 1.2 equiv R-OTf, 1.4 equiv LiOtBu, 2 mol % Pd(OAc)2, 5 mol % ligand, solvent (0.125 M), 98 °C, 16 h. Reactn Conditions for X = Br: 1.0 equiv 1, 2.0 equiv R–Br, 2.0 equiv NaOtBu, 2 mol % Pd2(dba)3, 4 mol % S-Phos, toluene (0.25 M), 110 °C.

b

Yields are isolated yields (average of two or more experiments) of material with >95% purity.

c

Yields as reported in reference 12.