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. 2022 Jul 26;87(15):10062–10072. doi: 10.1021/acs.joc.2c01045

Table 3. Brønsted Acid-Catalyzed Transannular Aminohalogenation on Lactams 5a–f.

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entry R1 R2 R3 compd yield 6a–f (%)a compd yield 7a–f (%)a
1 H H H 6a 98 (40 min) 7a 86 (16 h)
2 H F H 6b 98 (60 min) 7b 86 (16 h)
3 H H F 6c 68 (60 min) 7c 81 (16 h)
4 H H MeO 6db 41 (21 h) 7d 71 (23 h)
5 H H Me 6e 79 (3 h) 7e 85 (16 h)
6 Me H H 6fb 26 (72 h) 7f 46c (72 h)
a

Yield of pure products after flash column chromatography purification.

b

1.2 equiv of DBU was added after complete conversion of the starting material had been observed.

c

98% yield based on the recovered starting material.