Table 1.

RBF₃K synthesis with and without the use of ethylene glycol additive.

entry	product	X	% yield (time) a
1		CI	80 (20 min)
			77 (1.5 h)
2		CI	82 (2 h)
			68 (2 h)
3		Br	92 (20 min)
			68 (1 h)
4		Cl	52 b (30 min)
			47 (1.5 h)
5		CI	80 (3.5 h)
			0
6		CI	65 (1 h)
			52 (2 h)
7		CI	69 (1 h)
			53 (4.5 h)
8		CI	69 (25 min)
			64 (4 h)
9		CI	27 (45 min)
			0
			5 c
10		CI	66 d (84 h)
			43 e
			37 f (22 h)
			0 g (3 h)
		Br	0
11		CI	37 (50 min)
12		CI	76 (3 h)
			73 h (75 min)
13		CI	88 i (3 h)
14		CI	73 j (1 h)
			75k (4 h)
15		OMs	60 (4 h)
			0

^a1.5 mmol scale unless otherwise noted.

^bAs an inseparable mixture of internal salt and potassium trifluoroborate.

^cUsing (Me2N)2B- B(NMe2)2 as the borylating agent.

^d0 °C.

^ert.

^f50 °C.

^g80 °C.

^h65 °C, 7.6 mmol scale.

ⁱ65 °C.

^j13% coupled alcohol reduction product was also generated.

^k30% coupled alcohol reduction product was also generated.