镍催化硫酯转移反应合成芳基硫酯

doi:10.6023/cjoc202208035

摘要/Abstract

利用简单易得的硫酯作为硫源, 并且没有使用有毒的一氧化碳气体和硫醇, 实现了硫酯与芳基碘的镍催化官能团交换反应. 这种转移反应涉及与Ni(0)的两个氧化加成: 芳族酯的C—S键和卤代芳烃的C—I键, 两个生成的中间体经过官能团交换反应得到新的硫酯. 此外, 该方法条件温和, 操作简单, 为硫酯的合成提供了一条实用的途径.

关键词: 镍催化, 硫酯, 氧化加成

A nickel-catalyzed thioester transfer reaction using thioesters and aryl iodides was realized, utilizing simple and readily available thioesters as the sulfur source without smelly thiols and toxic carbon monoxide gas. The thioester transfer reaction involves two oxidative additions with Ni(0): C—S bond of the aromatic ester and C—I bond of haloarenes, and the two resulting intermediates undergoe a functional group exchange reaction to afford the new thioester. Furthermore, this approach features mild conditions and operational simplicity, providing a practical route for thioester synthesis.

Key words: Ni-catalysis, thioester, oxidative addition

引用此文

梁陆祺, 奚娟, 姜若楠, 杨艺, 孙丰钢, 张立志, 李新进, 刘会. 镍催化硫酯转移反应合成芳基硫酯[J]. 有机化学, 2023, 43(4): 1566-1573.

Luqi Liang, Juan Xi, Ruonan Jiang, Yi Yang, Fenggang Sun, Lizhi Zhang, Xinjin Li, Hui Liu. Ni-Catalyzed Aryl Thioester Synthesis via Thioester Transfer Reaction[J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1566-1573.

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Entry	Ni catalyst	Ligand	Solvent	Yield^a/%
1	NiBr₂(PPh₃)₂	L₁	Dioxane	NR
2	NiBr₂(PPh₃)₂	L₁	MeCN	NR
3	NiBr₂(PPh₃)₂	L₁	NMP	44
4	NiBr₂(PPh₃)₂	L₁	DMSO	56
5	NiBr₂(PPh₃)₂	L₁	DMF	25
6	NiBr₂(PPh₃)₂	L₁	NMP/DMSO (V∶V=1∶1)	77
7	NiBr₂•DME	L₁	NMP/DMSO (V∶V=1∶1)	61
8	NiBr₂(PPh₃)₂	L₁	NMP/DMSO (V∶V=1∶1)	68
9	NiCl₂•DME	L₁	NMP/DMSO (V∶V=1∶1)	69
10	NiBr₂(PPh₃)₂	L₂	NMP/DMSO (V∶V=1∶1)	26
11	NiBr₂(PPh₃)₂	L₃	NMP/DMSO (V∶V=1∶1)	59
12	NiBr₂(PPh₃)₂	L₄	NMP/DMSO (V∶V=1∶1)	66
13	NiBr₂(PPh₃)₂	DPPE	NMP/DMSO (V∶V=1∶1)	NR
14	NiBr₂(PPh₃)₂	L₁	NMP/DMSO (V∶V=1∶1)	34^b

Entry	Ni catalyst	Ligand	Solvent	Yield^a/%
1	NiBr₂(PPh₃)₂	L₁	Dioxane	NR
2	NiBr₂(PPh₃)₂	L₁	MeCN	NR
3	NiBr₂(PPh₃)₂	L₁	NMP	44
4	NiBr₂(PPh₃)₂	L₁	DMSO	56
5	NiBr₂(PPh₃)₂	L₁	DMF	25
6	NiBr₂(PPh₃)₂	L₁	NMP/DMSO (V∶V=1∶1)	77
7	NiBr₂•DME	L₁	NMP/DMSO (V∶V=1∶1)	61
8	NiBr₂(PPh₃)₂	L₁	NMP/DMSO (V∶V=1∶1)	68
9	NiCl₂•DME	L₁	NMP/DMSO (V∶V=1∶1)	69
10	NiBr₂(PPh₃)₂	L₂	NMP/DMSO (V∶V=1∶1)	26
11	NiBr₂(PPh₃)₂	L₃	NMP/DMSO (V∶V=1∶1)	59
12	NiBr₂(PPh₃)₂	L₄	NMP/DMSO (V∶V=1∶1)	66
13	NiBr₂(PPh₃)₂	DPPE	NMP/DMSO (V∶V=1∶1)	NR
14	NiBr₂(PPh₃)₂	L₁	NMP/DMSO (V∶V=1∶1)	34^b