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An oven-dried resealable Schlenk tube was capped with a rubber septum, cooled under an argon purge, charged with 1-hexene (0.19 mL, 1.5 mmol), and cooled to 0° C. A solution of 9-BBN in THF (3 mL, 1.5 mmol, 0.5 M) was added, the flask was stirred at 0° C. for 15 min, then warmed to room temperature and stirred for 5 h. 4-Chloroanisole (0.12 mL, 1.0 mmol) was added, the septum was removed, and palladium acetate (4.4 mg, 0.02 mmol, 2 mol %), ligand 2 (11.9 mg, 0.03 mmol, 3 mol %), and cesium fluoride (456 mg, 3.0 mmol) were added under a stream of argon. The septum was replaced and the flask was purged with argon for 30 s. Dioxane (2 mL) was added, the septum was removed, the tube was sealed with a teflon screw cap, and the mixture was stirred at rt for 2 min. The reaction mixture was then heated to 50° C. with stirring for 22 h, at which time GC analysis showed the aryl chloride had been completely consumed. The mixture was cooled to room temperature, diluted with ether (20 mL), and poured into a separatory funnel. The mixture was washed with 1 M aqueous NaOH (20 mL), the layers were separated, and the aqueous phase was extracted with ether (20 mL). The combined organic layers were dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The crude material was purified by flash chromatography to afford 170 mg (89%) of a colorless oil: 1H NMR (300 MHz, CDCl3) δ 7.09 (d, 2H, J=8.8 Hz), 6.82 (d, 2H, J=8.6 Hz), 3.78 (s, 3H), 2.54 (t, 2H, J=7.5 Hz), 1.54-1.60 (m, 2H), 1.28-1.35 (m, 6H), 0.88 (t, 3H, J=6.8 Hz); 13C NMR (125 MHz, CDCl3) δ 157.6, 135.0, 129.2, 113.6, 55.2, 35.0, 31.73, 31.70, 28.9, 22.6, 14.1; IR (neat, cm−1) 2926, 1513, 1243, 1038, 822. Anal Calcd for C13H20O: C, 81.20; 11, 10.48. Found: C, 81.19; H, 10.62.

1. customAn oven-dried resealable Schlenk tube was capped with a rubber septum
2. temperaturecooled under an argon
3. custompurge
4. temperaturewarmed to room temperature
5. stirringstirred for 5 h
6. customthe septum was removed
7. customthe flask was purged with argon for 30 s
8. additionDioxane (2 mL) was added
9. customthe septum was removed
10. customthe tube was sealed with a teflon
11. customscrew cap
12. stirringthe mixture was stirred at rt for 2 min
13. temperatureThe reaction mixture was then heated to 50° C.
14. stirringwith stirring for 22 h, at which time GC analysis
15. customhad been completely consumed
16. temperatureThe mixture was cooled to room temperature
17. additiondiluted with ether (20 mL)
18. additionpoured into a separatory funnel
19. washThe mixture was washed with 1 M aqueous NaOH (20 mL)
20. customthe layers were separated
21. extractionthe aqueous phase was extracted with ether (20 mL)
22. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
23. filtrationfiltered
24. concentrationconcentrated in vacuo
25. customThe crude material was purified by flash chromatography