. 2021 Nov 16;23(23):9068–9072. doi: 10.1021/acs.orglett.1c03321

Table 1. Optimization of the Reaction Conditions for the Alkylation of Vinyl Azide 3a with Alkyl Bromide 4a^a.

entry	solvent	changes	light (W)	yield (%)^c
1	MeCN	–	7	52
2	MeCN	60 °C, oil bath	–	31
3	MeCN	60 °C, microwave	–	32
4	DMA	–	7	27
5	DMF	–	7	64
6	DMF	HME instead B₁₂	7	26
7	DMF	–	3	28
8	DMF	30 min instead of 20 h	10	37
9^b	DMF	H₂O as an additive	7	82

General conditions: vinyl azide 3a (2.5 equiv), alkyl bromide 4a (0.25 mmol, 1.0 equiv), HME (2, 5 mol %), NH₄Cl (1.5 equiv), Zn (3.0 equiv), 18-crown-6 (1.5 equiv), H₂O (3 equiv), and solvent (0.1 M), 20 h, blue light (450 nm).

H₂O (1.5 equiv).

Yields based on HPLC measurements.

Table 1. Optimization of the Reaction Conditions for the Alkylation of Vinyl Azide 3a with Alkyl Bromide 4aa.

Table 1. Optimization of the Reaction Conditions for the Alkylation of Vinyl Azide 3a with Alkyl Bromide 4a^a.