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. Author manuscript; available in PMC: 2009 Jun 22.
Published in final edited form as: J Org Chem. 2005 Apr 15;70(8):3099–3107. doi: 10.1021/jo050022+

Table 3.

(a)

graphic file with name nihms-123274-t0037.jpg
Entry Substrate R R2 Product Yield(b) dr
1 11a Me graphic file with name nihms-123274-t0038.jpg 12a 43%(c) >20:1
2 11b Et 12b 37%(c) >20:1
3 11c t-Bu No Reaction ---
4 11d CO2Et 0%(d) ---
5 11e Ph graphic file with name nihms-123274-t0039.jpg 12c 62% >20:1
6 11e Ph graphic file with name nihms-123274-t0040.jpg 12d 60% >20:1
7 11e Ph graphic file with name nihms-123274-t0041.jpg 12e 61% >20:1
8 11e Ph graphic file with name nihms-123274-t0042.jpg 12f 37% >20:1
9 11e Ph graphic file with name nihms-123274-t0043.jpg 12g 29% >20:1
(a)

Conditions: 1.0 equiv alcohol, 2.0 equiv ArBr, 2.0 equiv NaOtBu, 1 mol % Pd2(dba)3, 2 mol % dpe-phos, THF (0.13-0.25 M), 65 °C.

(b)

Yields represent average isolated yields for two or more experiments.

(c)

A reductive workup was employed to facilitate removal of a ketone side product. See supporting information for complete details.

(d)

Heck arylation was observed.