Au(Ⅰ) Complexes as the Efficient Catalyst for Hydration of Alkynes at Room Temperature†

doi:10.7503/cjcu20150523

Abstract

Abstract:

A series of (1,1'-biphenyl)-2-yldi(adamantan-1-yl) phosphine ligands was synthesized to prepare eight kinds of Au(Ⅰ) complexes. And their catalytic performances were investigated in the hydration of alkynes using methanol as solvent. At room temperature, it was found that Au(Ⅰ) complexes containing the group of 3'-(pyrrolidin-1-ylcarbonyl) showed the excellent catalytic performance in the hydration of alkynes with the catalyst loading of 0.1%―0.3%(molar fraction, base on alkynes). The reaction parameters were further optimized for spreading the applied scope of the catalysts. Therefore, a mild catalytic system with good applicability was explored for the hydration of terminal and internal alkynes using less dosage of catalyst.

Key words: Au(Ⅰ) complex, Hydration of alkynes, Ketones, Catalytic reaction at room temperature

TrendMD:

WU Gongde, WANG Xiaoli, ZHANG Liming, JIANG Taineng. Au(Ⅰ) Complexes as the Efficient Catalyst for Hydration of Alkynes at Room Temperature^†[J]. Chem. J. Chinese Universities, 2015, 36(12): 2461.

Figures/Tables 6

References 30

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Entry	[Au]	[Ag]	Solvent	Yield^b(%)
1	Mor-DalPhosAuCl	—	Methanol	7
2	Me-DalPhosAuCl		Methanol	4
3	L1AuCl		Methanol	9
4	L2AuCl	—	Methanol	2
5	L3AuCl	—	Methanol	25
6	L4AuCl	—	Methanol	32
7	L5AuCl	—	Methanol	37
8	L6AuCl	—	Methanol	34
9	L7AuCl	—	Methanol	45
10	L8AuCl	—	Methanol	54
11	L8AuCl	AgNTf₂	Methanol	63^c
12	L8AuCl	AgNTf₂	THF	24
13	L8AuCl	AgNTf₂	Fluorobenzene	18
14	L8AuCl	AgNTf₂	MeCN	16
15	L8AuCl	AgNTf₂	Toluene	21
16	L8AuCl	AgNTf₂	Trifluoromethylbenzene	34
17	L8AuCl	AgNTf₂	Choloride benzene	26
18	L8AuCl	AgNTf₂	DCM	24

Entry	[Au]	[Ag]	Solvent	Yield^b(%)
1	Mor-DalPhosAuCl	—	Methanol	7
2	Me-DalPhosAuCl		Methanol	4
3	L1AuCl		Methanol	9
4	L2AuCl	—	Methanol	2
5	L3AuCl	—	Methanol	25
6	L4AuCl	—	Methanol	32
7	L5AuCl	—	Methanol	37
8	L6AuCl	—	Methanol	34
9	L7AuCl	—	Methanol	45
10	L8AuCl	—	Methanol	54
11	L8AuCl	AgNTf₂	Methanol	63^c
12	L8AuCl	AgNTf₂	THF	24
13	L8AuCl	AgNTf₂	Fluorobenzene	18
14	L8AuCl	AgNTf₂	MeCN	16
15	L8AuCl	AgNTf₂	Toluene	21
16	L8AuCl	AgNTf₂	Trifluoromethylbenzene	34
17	L8AuCl	AgNTf₂	Choloride benzene	26
18	L8AuCl	AgNTf₂	DCM	24

Entry	Yield(%)	Entry	Yield(%)
1	92^b	6	95^c
2	95 ^b	7	98 ^c
3	93 ^b	8	98 ^c
4	84 ^b	9	97 ^c
5	71 ^b	10	94 ^c

Entry	Yield(%)	Entry	Yield(%)
1	92^b	6	95^c
2	95 ^b	7	98 ^c
3	93 ^b	8	98 ^c
4	84 ^b	9	97 ^c
5	71 ^b	10	94 ^c