手性P,N,N-配体/钯催化的不对称烯丙基取代反应

doi:10.6023/cjoc202306004

摘要/Abstract

P,N,N-配体是近年来发展起来的在不对称催化反应中具有广泛应用的一类手性配体. 将手性P,N,N-配体应用于钯催化不对称烯丙基取代反应研究. 结果表明, 在较温和条件下, 含C、N和O的各类亲核试剂均能顺利发生反应, 获得良好的产率和对映选择性(产率高达97%, 93% ee).

关键词: P,N,N-配体, 不对称烯丙基取代, 钯

Chiral P,N,N-ligands are a new type of ligands developed in recent years, which have been widely used in asymmetric catalytic reactions. In this study, chiral P,N,N-ligands were applied to palladium-catalyzed asymmetric allylic substitution reactions. The results showed that under mild conditions, various nucleophiles containing carbon, nitrogen and oxygen could react smoothly, achieving good yields (up to 97% yield) and enantioselectivities (up to 93% ee).

Key words: P,N,N-ligands, asymmetric allylic substitution, palladium

引用此文

秦浩, 侯传金, 梁丁化, 何心伟, 李玲, 胡向平. 手性P,N,N-配体/钯催化的不对称烯丙基取代反应[J]. 有机化学, 2024, 44(1): 282-290.

Hao Qin, Chuanjin Hou, Dinghua Liang, Xinwei He, Ling Li, Xiangping Hu. Chiral P,N,N-Ligands for Pd-Catalyzed Asymmetric Allylic Substitutions[J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 282-290.

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Entry	[Pd]	Base	Solvent	Temperature/℃	Yield^b/%	ee^c
1	[Pd(C₃H₅)Cl]₂	BSA, NaOAc	Toluene	50	71	82
2	Pd(OAc)₂	BSA, NaOAc	Toluene	50	28	33
3	Pd₂(dba)₃	BSA, NaOAc	Toluene	50	NR
4	Pd[P(C₆H₅)₃]₄	BSA, NaOAc	Toluene	50	35	48
5	[Pd(C₃H₅)Cl]₂	BSA, KOAc	Toluene	50	30	82
6	[Pd(C₃H₅)Cl]₂	BSA, K₂CO₃	Toluene	50	86	72
7	[Pd(C₃H₅)Cl]₂	BSA, Na₂CO₃	Toluene	50	17	77
8	[Pd(C₃H₅)Cl]₂	BSA	Toluene	50	56	79
9	[Pd(C₃H₅)Cl]₂	BSA, NaOAc	Toluene	80	84	35
10	[Pd(C₃H₅)Cl]₂	BSA, NaOAc	Toluene	r.t.	61	82
11	[Pd(C₃H₅)Cl]₂	BSA, NaOAc	THF	50	90	91
12	[Pd(C₃H₅)Cl]₂	BSA, NaOAc	CH₃CN	50	90	55
13	[Pd(C₃H₅)Cl]₂	BSA, NaOAc	1,4-Dioxane	50	76	85
14	[Pd(C₃H₅)Cl]₂	BSA, NaOAc	CH₃OH	50	NR
15	[Pd(C₃H₅)Cl]₂	BSA, NaOAc	Et₂O	50	95	73
16	[Pd(C₃H₅)Cl]₂	BSA, NaOAc	CH₂Cl₂	50	70	86

Entry	[Pd]	Base	Solvent	Temperature/℃	Yield^b/%	ee^c
1	[Pd(C₃H₅)Cl]₂	BSA, NaOAc	Toluene	50	71	82
2	Pd(OAc)₂	BSA, NaOAc	Toluene	50	28	33
3	Pd₂(dba)₃	BSA, NaOAc	Toluene	50	NR
4	Pd[P(C₆H₅)₃]₄	BSA, NaOAc	Toluene	50	35	48
5	[Pd(C₃H₅)Cl]₂	BSA, KOAc	Toluene	50	30	82
6	[Pd(C₃H₅)Cl]₂	BSA, K₂CO₃	Toluene	50	86	72
7	[Pd(C₃H₅)Cl]₂	BSA, Na₂CO₃	Toluene	50	17	77
8	[Pd(C₃H₅)Cl]₂	BSA	Toluene	50	56	79
9	[Pd(C₃H₅)Cl]₂	BSA, NaOAc	Toluene	80	84	35
10	[Pd(C₃H₅)Cl]₂	BSA, NaOAc	Toluene	r.t.	61	82
11	[Pd(C₃H₅)Cl]₂	BSA, NaOAc	THF	50	90	91
12	[Pd(C₃H₅)Cl]₂	BSA, NaOAc	CH₃CN	50	90	55
13	[Pd(C₃H₅)Cl]₂	BSA, NaOAc	1,4-Dioxane	50	76	85
14	[Pd(C₃H₅)Cl]₂	BSA, NaOAc	CH₃OH	50	NR
15	[Pd(C₃H₅)Cl]₂	BSA, NaOAc	Et₂O	50	95	73
16	[Pd(C₃H₅)Cl]₂	BSA, NaOAc	CH₂Cl₂	50	70	86