. Author manuscript; available in PMC: 2010 Oct 1.

Published in final edited form as: Org Lett. 2009 Oct 1;11(19):4330–4333. doi: 10.1021/ol901669k

Table 2.

Optimization of Reaction Conditions for the Preparation of Potassium 4-Azidophenyltrifluoroborate (1b)^a


entry	CuX	ligand	base	reaction time (h)	conversion yield (%)^b
1	CuI	a	K₂CO₃	24	66
2	CuI	b	K₂CO₃	5	98
3	CuI	c	K₂CO₃	16	100
4	CuI	d	K₂CO₃	24	81
5	CuI	e	K₂CO₃	15	100
6	CuI	f	K₂CO₃	1	100 (88)^c
7	CuI	g	K₂CO₃	24	trace
8	CuI	h	K₂CO₃	48	68
9	CuI^d	f	K₂CO₃	2	100 (89)^c
10	CuBr	f	K₂CO₃	1	100 (92)^c
11	CuBr	f	Cs₂CO₃	0.5	100 (94)^c
12^e	CuBr	f	Cs₂CO₃	2.5	100

All reactions were performed on a 0.05 mmol scale in 0.5 mL of DMSO-d₆ in an NMR tube.

Percent conversions were determined by ¹H NMR of the reaction mixtures. The conversion yield was based on the integration of peaks at 7.14 (1a-I) ppm and 6.85 (1b) ppm, respectively.

Reactions were performed on a 0.1 mmol scale and isolated yields are reported.

5 mol % of CuI was used.

Reaction was performed in DMF-d₇.