Nickel-Catalyzed Borylation of Aryl Nonaflates for the Efficient Synthesis of Arylboronates via C—O Bond Functionalization

doi:10.6023/cjoc202507010

Abstract

Nickel-catalyzed borylation of aryl nonaflates with B₂pin₂ could be realized, which proceeded effectively by means of C—O bond functionalization to afford a wide variety of valuable arylboronates in moderate to excellent yields with good functionality compatibility. In addition, the gram-scale synthesis and the application of the approach in the late-stage elaboration of aryl nonaflate derived from pterostilbene could also be achieved.

Key words: nickel catalysis, borylation, aryl nonaflates, arylboronates, C—O bond functionalization

Cite this article

Liang Yuan, Gui Chao, Wang Wenwen, Chu Xueqiang, Xu Hao, Shen Zhiliang. Nickel-Catalyzed Borylation of Aryl Nonaflates for the Efficient Synthesis of Arylboronates via C—O Bond Functionalization[J]. Chinese Journal of Organic Chemistry, 2026, 46(1): 207-214.

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Entry	Catalyst	Yield/%	Entry	Catalyst	Yield/%
1	CoBr₂	<5	12	Ni(PCy₃)₂Cl₂	71
2	CrCl₃	0	13	NiCl₂•dppf	59
3	CuI	0	14	NiCl₂•dppp	17
4	Cu(OAc)₂	0	15	Ni(PPh₃)₂Br₂	87
5	FeCl₃	0	16	Ni(PPh₃)₂Cl₂	95 (75)^c
6	NiCl₂	<5	17	NiCl₂	85^d
7	NiBr₂	<5	18	Ni(cod)₂	72^d
8	NiI₂	<5	19	—	0
9	NiCl₂•DME	<5	20	Ni(PPh₃)₂Cl₂	0^e
10	Ni(acac)₂	<5	21	Ni(PPh₃)₂Cl₂	7^f
11	Ni(cod)₂	0

Entry	Catalyst	Yield/%	Entry	Catalyst	Yield/%
1	CoBr₂	<5	12	Ni(PCy₃)₂Cl₂	71
2	CrCl₃	0	13	NiCl₂•dppf	59
3	CuI	0	14	NiCl₂•dppp	17
4	Cu(OAc)₂	0	15	Ni(PPh₃)₂Br₂	87
5	FeCl₃	0	16	Ni(PPh₃)₂Cl₂	95 (75)^c
6	NiCl₂	<5	17	NiCl₂	85^d
7	NiBr₂	<5	18	Ni(cod)₂	72^d
8	NiI₂	<5	19	—	0
9	NiCl₂•DME	<5	20	Ni(PPh₃)₂Cl₂	0^e
10	Ni(acac)₂	<5	21	Ni(PPh₃)₂Cl₂	7^f
11	Ni(cod)₂	0

镍催化的芳基全氟丁基磺酸酯通过碳-氧键官能化的硼化反应高效合成芳基硼酸酯