Nature Communications

Table 1 Optimization of reaction conditions

From: Regioselective radical α-borylation of α,β-unsaturated carbonyl compounds for direct synthesis of α-borylcarbonyl molecules


Entry	LB-BH₃	Initiator	RSH (x mol%)	3a Yield (%)^b
1	2a	AIBN	tert-dodecanethiol (20)	49 (39)^d
2	2a	AIBN	tert-dodecanethiol (50)	81^c
3	2a	AIBN	PhSH (20)	77
4	2a	AIBN	4-MeOC₆H₄SH (20)	75
5	2a	AIBN	4-CO₂MeC₆H₄SH (20)	73
6	2a	AIBN	MeO₂CCH₂SH (20)	80
7	2b	AIBN	PhSH (20)	89
8	2c	AIBN	PhSH (20)	70
9	2d	AIBN	PhSH (20)	67
10	2e	AIBN	PhSH (20)	0 (95)^e
11	2 f	AIBN	PhSH (20)	0 (98)^e
12	2a	AIBN	--	0 (83)^d
13^f	2a	TBHN	tert-dodecanethiol (50)	67 (17)^d
14^f	2a	TBHN	PhSH (20)	60
15	2a	--	tert-dodecanethiol (50)	0 (98)^d
16	2a	--	PhSH (20)	0 (88)^d

^aReaction conditions: 2 (0.2–0.3 mmol), 1a (1.2 equiv), initiator (20 mol%), RSH (x mol%), CH₃CN (2 ml), 80 °C for 12 h
^bNMR yield using tetrachloroethane as an internal standard
^cIsolated yield
^dRecovery yield of 2a is shown in parentheses
^eRecovery yield of 1a is shown in parentheses
^fThe reaction was conducted at 50 °C

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