BMC Chemistry

Table 1 Pd-catalyzed borylation of 4-chloroanisole (1a) under various conditions

From: Palladium-catalyzed borylation of aryl (pseudo)halides and its applications in biaryl synthesis


Entry	Catalyst	Solvent	Base	Temp. (°C)	Time (h)	Yield^a (%)
1	Pd(PPh₃) ^b₄	DMSO	KOAc	80	8	Trace^c
2	Pd(PPh₃)₄/PCy ^b₃	Dioxane	KOAc	80	8	72^c
3	PdCl₂(PPh₃) ^b₂	DMF	K₃PO₄	80	8	12^c
4	PdCl₂(dppf)^b	DMF	K₃PO₄	80	8	Trace^c
5	PdCl₂(dppf)^b	DMSO	KOAc	80	8	Trace^c
6	Pd₂dba₃/PCy ^b₃	Dioxane	KOAc	110	8	67^c
7	Pd₂dba₃/XPhos^b	Dioxane	KOAc	110	8	81^c
8	Pd₂dba₃/SPhos^b	Dioxane	KOAc	110	8	48^c
9	Pd(OAc)₂/PCy ^b₃	Dioxane	KOAc	110	2	69^c
10	Pd(OAc)₂/XPhos^b	Dioxane	KOAc	110	2	76^c
11	Pd(OAc)₂/SPhos	Dioxane	KOAc	RT	48	42
12	9a	THF	KOAc	RT	2	Trace^d
13	9a	EtOH	KOAc	RT	2	13^d
14	9b	THF	KOAc	RT	2	23^d
15	9b	EtOH	KOAc	RT	2	66^d
16	10a	THF	KOAc	RT	2	21^d
17	10a	EtOH	KOAc	RT	2	12^d
18	10b	THF	KOAc	RT	2	93^d
19	10b	EtOH	KOAc	RT	2	35
20	10b	THF	K₃PO₄	RT	1	87^e, 98^f

Reaction conditions: 4-chloroanisole (1a; 1.0 mmol), B₂pin₂ (3.0 mmol), base (3.0 mmol), catalyst (2.0 mol%), ligand (4.0 mol%), solvent (2 mL)
^aIsolated yield
^bNo reaction occurred at room temperature
^cSealed tube
^dB₂pin₂ (3.0 mmol), precatalyst (2.0 mol%)
^eB₂pin₂ (3.0 mmol), precatalyst (2.0 mol%), K₃PO₄ (2.0 mmol)
^fB₂pin₂ (1.2 mmol), precatalyst (1.0 mol%)

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ISSN: 2661-801X

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