Reusable polymer-supported copper catalyst for one-pot synthesis of 1-alkyl- and 1-aryl-1,2,3-triazoles: green, simple, and effective

Figures & data

short-legendScheme 1. Polymer-supported copper catalyst for one-pot synthesis of 1,2,3-triazoles.

Table 1. Screening of reaction parameters for one-pot synthesis of triazoles using benzyl chloride as substrate.^a

Entry	Solvent	Base	Catalyst loading (mol%)	Time (h)	Yield^b (%)
1	DMSO/H2O (2:1)	Et3N	10	24	56
2	^tBuOH/H2O (1:1)	Et3N	10	24	72
3	CH2Cl2/H2O (1:1)	Et3N	10	24	35
4	PEG 400	Et3N	10	12	82
5	H2O	Et3N	10	24	67
6	PEG 400/H2O (1:1)	Et3N	10	8	87
7	PEG 400/H2O (1:1)	–	10	8	44
8	PEG 400/H2O (1:1)	Bu3N	10	8	76
9	PEG 400/H2O (1:1)	Na2CO3	10	8	84
10	PEG 400/H2O (1:1)	NaOH	10	8	62
11	PEG 400/H2O (1:1)	Et3N	5	12	65
12	PEG 400/H2O (1:1)	Et3N	–	24	Trace
^aReaction conditions: benzyl chloride (1 mmol), NaN3 (1.2 mmol), phenylacetylene (1 mmol), solvent (4 ml), and room temperature.
^bIsolated yields.

Table 2. Synthesis of 1,4-disubstituted 1-alkyl-1,2,3-triazoles.^a

Entry	Substrate	Temperature (°C)	Time (h)	Yield^b (%)
1	PhCH2Cl	rt	8	87, 87, 85, 85, 67^c
2	PhCH2Br	rt	8	89
3	p-Me- PhCH2Cl	rt	8	85
4	p-F- PhCH2Cl	rt	8	90
5	p-CN- PhCH2Cl	rt	8	92
6	p-NO2- PhCH2Cl	rt	8	94
7	CH2=CHCH2Cl	rt	8	72
8	CH2=CHCH2Br	rt	8	76
9	C2H5Br	rt	12	73
10	C4H9Br	rt	12	75
11	C6H5I	rt	24	–
^aReaction conditions: substrate (1 mmol), NaN3 (1.2 mmol), phenylacetylene (1 mmol), PEG 400/H2O (4 ml, 1:1), Et3N (1 mmol), A21-CuI (77 mg, 10 mol%), and room temperature.
^bIsolated yields.
^cCatalyst was reused.

short-legendScheme 2. One-pot two-step synthesis of 1-phenyl triazoles.

Table 3. A21-CuI catalyzed the one-pot synthesis of 1-aryl 1,2,3-triazoles.^a

Entry	Arylboronic acid	Product	Time (h)	Yield^b (%)
1			8	89, 89, 87, 88, 85, 82, 74^c
2			8	91
3			6	95
4			12	73
5			24	65
6			24	76
7			8	92
^aReaction conditions: arylboronic acid (1 mmol), NaN3 (1.2 mmol), phenylacetylene (1.1 mmol), MeOH (4 ml), A21-CuI (77 mg, 10 mol%), and room temperature.
^bIsolated yields.
^cCatalyst was reused.