. 2022 Jul 15;41(15):2154–2169. doi: 10.1021/acs.organomet.2c00246

Table 3. Cycloaddition of Benzyl Azide and Phenylacetylene Catalyzed by [Cu₂(μ-Br)₂(^tBuImCH₂pyCH₂NEt₂)]₂ (5) at Low Catalyst Loading^a.

entry	T (K)	solvent	5 (mol %)	t (h)	conversion (%)^b	TON	TOF (h^–1)
1	298	neat	0.25	0.08	56	224	2800
2	298	neat	0.05	0.5	50	1000	2000
3	298	neat	0.05	3	88	1760	600
4	298	neat	0.005	24	96	19,200	800
5	323	neat	0.005	24	99	19,800	820
6	298	CH₃CN	0.005	24	0	0	0
7	323	CH₃CN	0.005	48	80	16,000	300
8	298	neat	0.0025	24	66	26,400	1100
9	298	neat	0.0025	48	82	32,800	680
10	323	neat	0.0025	24	90	36,000	1500
11	323	neat	0.0025	48	98	39,200	820

Reaction conditions: benzyl azide (0.5 mmol), phenylacetylene (0.5 mmol), solvent (0.5 mL).

Conversion relative to benzyl azide and selectivities determined by GC using mesitylene as internal standard.

Table 3. Cycloaddition of Benzyl Azide and Phenylacetylene Catalyzed by [Cu2(μ-Br)2(tBuImCH2pyCH2NEt2)]2 (5) at Low Catalyst Loadinga.