TABLE 1.

Efficient, Mild Route to α-Fluoro Acrylonitriles

entry	aldehyde	temp	product: yield,a%E/Z ratiob	=C(CN)F: δ (ppm);cJ (Hz)	lit:d yield, E/Z ratio
1		rt	12: 98%, 15:85	-122.1; 36.6	--
		-78 °C	12: 97%, 8:92	-122.5; 15.3
2		rt	13: 93%, 19:81	-121.9; 35.2	54%, 66:3310
				-122.6; 17.6	53%, 21:7911
3		rt	14: 95%, 16:84	-126.2; 36.6	52%, 50:509
				-127.1; 18.3	50%, 32:6811
4		rt	15: 91%, 37:63	-122.3; 15.3	--
		-78 °C	15: 91%, 27:73	-124.1; 36.6
5		rt	16: 94%, 17:83	-120.4; 15.3	--
				-123.0; 36.6
6		rt	17: 72%, 17:83	-115.3; 15.3	45%, 33:679
				-115.7; 33.6
7		rt	18: 60%, 15:85	-117.0; 12.2	62%, 38:629
				-120.1; 30.5
8		rt	19: 91%, 16:84	-118.8; 15.3	--
				-119.8; 36.6
9		rt	20: 96%, 17:83	-122.8; 29.4	--
				-129.0; 11.7
10		rt	21: 59%, 18:82	-117.9; 33.6	--
				-125.3; 15.3
11		rt	22: 86%, 20:80	-119.2; 33.6	--
				-125.9; 12.2
12		rt	23: 92%, 17:83	-128.5; 35.2	--
				-129.6; 17.6
13		rt	24: 81%, 17:83	-126.6; 30.5	38%, 60:4010
				-127.7; 12.2	45%, 44:5611
14	n-heptyl-CHO	rt	25: 97%, 23:77	-123.9; 11.8	Lit. data for n-heptanal:e 30%, 30:7010 50%, 26:7411
		-78 °C	25: 90%, 16:84	-125.8; 35.2
15		rt	26: 80%, 23:77	-122.6; 14.7	51%, 26:7411
		-78 °C	26: 81%, 12:88	-124.2; 32.3
16		rt	27: 76%, 15:85	-122.8; 15.3	--
		-78 °C	27: 77%, 8:92	-125.6; 30.5

^aYields of isolated, purified products (reactions were performed under similar conditions but were not optimized for individual cases).

^bRelative ratio of diastereomers in the crude reaction mixture determined by ¹⁹F NMR prior to isolation. No change in ratio was observed after purification.

^cReferenced to CFCl₃ as internal standard.

^dWhere applicable, literature data and references are included for comparison.

^eSince no literature data for n-octanal are available, data for n-heptanal are included for comparison.