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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 9.

Entry Alcohol R2-Br Product Yield(b) dr
1 graphic file with name nihms-123274-t0067.jpg graphic file with name nihms-123274-t0068.jpg graphic file with name nihms-123274-t0069.jpg 60% 10:1
2 graphic file with name nihms-123274-t0070.jpg graphic file with name nihms-123274-t0071.jpg graphic file with name nihms-123274-t0072.jpg 70% >20:1
3 graphic file with name nihms-123274-t0073.jpg graphic file with name nihms-123274-t0074.jpg 40% >20:1
4 graphic file with name nihms-123274-t0075.jpg graphic file with name nihms-123274-t0076.jpg graphic file with name nihms-123274-t0077.jpg 53% >20:1
5(a)(b) graphic file with name nihms-123274-t0078.jpg graphic file with name nihms-123274-t0079.jpg 0%(c) --
(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)

Oxidation of the alcohol substrate to 2-allylcyclopentanone was observed.