Scope of hydromonofluoromethylation of dienes with 2 ^a.

Entry	1: substituent (●)	2	Time (d)	3	Yield (%)	ee (%)
1	1a: C6H5	2a	3	3a	86	96
2	1b: 4-MeC6H4	2a	4	3b	99	94
3	1c: 4-MeOC6H4	2a	3	3c	97	97
4b	1d: 3-MeOC6H4	2a	3	3d	86	98
5b	1e: 2-MeOC6H4	2a	3	3e	93	98
6	1f: 3,5-MeO2C6H3	2a	3	3f	98	99
7b	1g: 4-Me2NC6H4	2a	4	3g	48	93
8	1h: 4-CH2 CH(CH2)2C6H4	2a	3	3h	68	95
9	1i: 4-CF3C6H4	2a	4	3i	94	97
10	1j: 4-EtO2CC6H4	2a	3	3j	82	96
11	1k: 4-CNC6H4	2a	3	3k	90	98
12	1l: 4-COMeC6H4	2a	3	3l	90	98
13	1m: 4-CHOC6H4	2a	3	3m	71	90
14	1n: 4-ClC6H4	2a	4	3n	87	97
15	1o: 4-FC6H4	2a	4	3o	74	99
16c	1p: 3-FC6H4	2a	4	3p	92	96
17c	1q: 2-FC6H4	2a	4	3q	99	94
18	1r: 3,5-(CF3)2C6H3	2a	3	3r	49	95
19	1s: 2-naphthyl	2a	3	3s	97	99
20c	1t: 1-naphthyl	2a	3	3t	98	91
21b	1u: 2-furyl	2a	3	3u	85	93
22b	1v: 2-thienyl	2a	3	3v	98	98
23	1w: (E)-Ph-CH CH	2a	5	3w	99	97
24d	1x: n-C5H11	2a	3	3x	67	93
25d	1y: PhCH2CH2	2a	5	3y	81	90
26d		2a	4	3z	69	94
27b	1a: C6H5	2b	5	3aa	94	97
28b	1a: C6H5	2c	5	3ab	99	95

^aConditions: 1 (0.375 mmol), 2 (0.25 mmol), and EtOH (2.5 mL), at rt, unless otherwise noted; yields of the isolated products are reported; the ee values were determined by chiral HPLC analysis. For 3a, 3c, 3o, and 3s: Ni(COD)₂ (5 mol%) and L8 (5.5 mol%) were used; for the others: Ni(COD)₂ (10 mol%) and L8 (11 mol%) were used.

^bAt 50 °C.

^cAt 60 °C.

^dAt 70 °C.