Nature Communications

Table 1 Optimization of the reaction conditions^a

From: Bifunctional iron-catalyzed alkyne Z-selective hydroalkylation and tandem Z-E inversion via radical molding and flipping


Entry	Catalyst 1	Catalyst 2	Ligand	Solvent	Yield^b	3a/4a^c
1^d	FeCl₃	–		CH₃CN	Trace	–
2^e	FeCl₃	FeCl₂•4H₂O		CH₃CN	36%	66:34
3	FeCl₃	FeCl₂•4H₂O		CH₃CN	62%	72:28
4	FeCl₃	FeCl₂•4H₂O		CH₂Cl₂	25%	54:46
5	FeCl₃	FeCl₂•4H₂O		Acetone	Trace	–
6	FeCl₃	FeCl₂•4H₂O		DMSO	Trace	–
7	FeCl₃	FeCl₂•4H₂O	L4	CH₃CN	87%	81:19
8	FeCl₃	FeCl₂•4H₂O	L5	CH₃CN	86%	86:14
9	FeCl₃	FeCl₂•4H₂O	L6	CH₃CN	90%	90:10
10	–	FeCl₂•4H₂O		CH₃CN	20%	72:28
11^f	FeCl₃	FeCl₂•4H₂O		CH₃CN	0	–
12^g	FeCl₃	FeCl₂•4H₂O		CH₃CN	Trace	–

^aReaction conditions: 1a (0.3 mmol), 2a (3 mmol), catalyst 1 (0.001 equiv.), catalyst 2 (0.5 equiv.), ligand (0.5 equiv.), and CH₃CN (3 mL) under N₂ and irradiation of a 30 W 365 nm LED for 48 h.
^bIsolated yields.
^cDetected by ¹H NMR.
^dCatalyst 1 (0.01 equiv.).
^eCatalyst 1 (0.01 equiv.), catalyst 2 (0.1 equiv.).
^fNo light.
^g405 nm LED. 1a–4a refer to the compounds shown in the chemical equation.

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