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. Author manuscript; available in PMC: 2013 Sep 21.
Published in final edited form as: Org Lett. 2012 Sep 4;14(18):4814–4817. doi: 10.1021/ol302124j

Table 1.

Trifluoroborate Synthesis from Aryl Chlorides and Bromides

graphic file with name nihms405477u2.jpg
entry X product time (h) % isolated yield
1 Cl graphic file with name nihms405477t1.jpg 5 94, 94a, 93b
2 Cl graphic file with name nihms405477t2.jpg 3 96, 86b, 93c
3 Cl graphic file with name nihms405477t3.jpg 7 39, 68b
4 Br graphic file with name nihms405477t4.jpg 3.5 56, 64b
5 Cl graphic file with name nihms405477t5.jpg 2.5 97, 91b, 98d
6 Cl graphic file with name nihms405477t6.jpg 5.5 85, 81b
7 Cl graphic file with name nihms405477t7.jpg 2.5 92, 91b
8 Cl graphic file with name nihms405477t8.jpg 3 97, 98a
98b, 87e, 85f
9 Br graphic file with name nihms405477t9.jpg 6 90, 94b
10 Cl graphic file with name nihms405477t10.jpg 5 84, 97b
11 Br graphic file with name nihms405477t11.jpg 5 96g, 87b,g
12 Br graphic file with name nihms405477t12.jpg 3 84, 97b
13 Br graphic file with name nihms405477t13.jpg 6 91, 94b
14 Br graphic file with name nihms405477t14.jpg 7 4, 27b
15 Br graphic file with name nihms405477t15.jpg 26 75, 80b
16 Cl graphic file with name nihms405477t16.jpg 22 81, 53b
17 Cl graphic file with name nihms405477t17.jpg 22 43
18 Cl graphic file with name nihms405477t18.jpg 22 0

General conditions: 0.5 mol % of 1, 1.0 mol % of 2, 3.0 equiv of KOAc, 3.0 equiv of B2(NMe2)4, MeOH (0.2 M), 60 °C for time indicated.

a

0.5 M MeOH.

b

Yield from previous method with B2(OH)4 as boron source (ref 15).

c

Reaction run in a round bottom flask with reflux condensor under argon.

d

10 mmol reaction run under general reaction conditions.

e

(1)5.0 mol % of Pd(OAc)2, 10 mol % of 2, 3.0 equiv of KOAc, 60 °C in 2 mL MeOH for 20 min. (2) 3.0 equiv of B2(NMe2)4 dissolved in 5.5 mL of MeOH, 1-chloro-4-fluorobenzene, 60 °C for time indicated.

f

Yield of isolated boronic acid.

g

From the acetonide.