Copper-Catalyzed Cross-Coupling of Aryldiazoacetates with Bis[(pinacolato)boryl]methane

doi:10.6023/cjoc202301027

Abstract

The copper-catalyzed cross-coupling reaction of 1,1-bis[(pinacolato)boryl]methane with α-diazophenylacetate as carbene precursor was reported, leading to the construction of C(sp³)—C(sp³) bond. Reaction optimization experiments showed that Monophos ligand was critical for the success of this reaction. In situ oxidation afforded the corresponding primary alcohols instead of the relatively unstable boronates. The reaction has high efficiency and good functional group compatibility. The two-step transformation represents a formal hydroxymethylation of diazoacetates.

Key words: copper catalysis, C(sp³)—C(sp³) bond formation, diazo compounds, bis[(pinacolato)boryl]methane

Cite this article

Zhicheng Bao, Muyao Li, Jianbo Wang. Copper-Catalyzed Cross-Coupling of Aryldiazoacetates with Bis[(pinacolato)boryl]methane[J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1808-1814.

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Entry	[Cu]	Ligand	Base	Solvent	Yield^b/ %
1	CuCl	Ligand^c	LiO^tBu	Toluene	0
2	CuCl	L1	LiO^tBu	Toluene	24
3	CuCl	L2~L5	LiO^tBu	Toluene	0
4	CuCl	L1	Base^d	Toluene	0
5	CuCl	L1	LiO^tBu	THF	0
6	CuCl	L1	LiO^tBu	DCE	0
7	CuCl	L1	LiO^tBu	m-Xylene	18
8	CuCl	L1	LiO^tBu	Chlorobenzene	14
9	CuCl	L1	LiO^tBu	Trifluorotoluene	8
10^e	CuCl	L1	LiO^tBu	Toluene	38
11^f	CuCl	L1	LiO^tBu	Toluene	52
12	CuBr	L1	LiO^tBu	Toluene	30
13	CuI	L1	LiO^tBu	Toluene	24
14	CuTC	L1	LiO^tBu	Toluene	38
15	Cu(MeCN)₄PF₆	L1	LiO^tBu	Toluene	48
16	CuCl₂	L1	LiO^tBu	Toluene	48
17^g	CuCl	L1	LiO^tBu	Toluene	54
18^h	CuCl	L1	LiO^tBu	Toluene	74

Entry	[Cu]	Ligand	Base	Solvent	Yield^b/ %
1	CuCl	Ligand^c	LiO^tBu	Toluene	0
2	CuCl	L1	LiO^tBu	Toluene	24
3	CuCl	L2~L5	LiO^tBu	Toluene	0
4	CuCl	L1	Base^d	Toluene	0
5	CuCl	L1	LiO^tBu	THF	0
6	CuCl	L1	LiO^tBu	DCE	0
7	CuCl	L1	LiO^tBu	m-Xylene	18
8	CuCl	L1	LiO^tBu	Chlorobenzene	14
9	CuCl	L1	LiO^tBu	Trifluorotoluene	8
10^e	CuCl	L1	LiO^tBu	Toluene	38
11^f	CuCl	L1	LiO^tBu	Toluene	52
12	CuBr	L1	LiO^tBu	Toluene	30
13	CuI	L1	LiO^tBu	Toluene	24
14	CuTC	L1	LiO^tBu	Toluene	38
15	Cu(MeCN)₄PF₆	L1	LiO^tBu	Toluene	48
16	CuCl₂	L1	LiO^tBu	Toluene	48
17^g	CuCl	L1	LiO^tBu	Toluene	54
18^h	CuCl	L1	LiO^tBu	Toluene	74

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