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Wirth, T.; Singh, F. V., Science of Synthesis Knowledge Updates, (2017) 1, 417.
Various catalytic approaches using transition-metal salts for the aminochlorination of alkenes have been reported.[42] In 2006, Li and co-workers developed an iron-catalyzed aminochlorination of (arylmethylene)cyclopropanes 33 using N,N-dichloro-4-toluenesulfonamide (34) as source of both chlorine and nitrogen (Scheme 18). Reactions are carried out in acetonitrile at room temperature and reaction products 35 are isolated in good yields.[43] Other transition-metal salts were investigated as catalysts, but iron(III) chloride was found to be the most efficient for these aminochlorinations. The same approach has been successfully applied for the aminochlorination of (arylvinylidene)cyclopropanes.[43]
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M8 | Me8 | Meeee (%) | Mee |
---|---|---|---|
M | Me | 88 | [88] |
M | 8-Mee | 88 | [88] |
M | 8-MeMM8M8 | 88 | [88] |
M | 8,8-(MeM)8M8M8 | 88 | [88] |
M | 8,8,8-(MeM)8M8M8 | 88 | [88] |
M | 8-eeeeeeee | 88 | [88] |
Me | Me | 88 | [88] |
8-Mee | 8-Mee | 88 | [88] |
8-MeMM8M8 | 8-MeMM8M8 | 88 | [88] |
Meeeeeeeeee, Meeeeee eee ee-eeeeeee eeee eeeeeeeee eeeeeeeee-eeeeeeeee eeeeeeeeeeeeee eeeeeeeeeeeeeeeee ee eeeeeeeeeee eeeeeee eeeeee/eeeeeeeeee 88 eeeee M-eeeeeeeeeeeeeeeee ee eee eeeeee ee eeeeeeee eee 88 eee% ee eee(eeeeeeeeeeee)eeeeeeeeeeeeeeeee(MM) ee eeeeeeee (Meeeee 88). Meeeeeeee eee eeeeeee eee ee eeeeeeeeeeeeeee, eee eeeeee eeeeee 88 eee eeeeeeee ee eeee ee eeeeeeeee eeeeee.[88]
Meeeee 88 Meeeeeeee-Meeeeeeee Meeeeeeeeeeeee Meeeeeeeeeeeeeeee ee Meeeeeeeeee Meeeeee Meeee M-Meeeeeeeeeeeeeeee ee eee Meeeeeee Meeeee[88]
M8 | M8 | M8 | M8 | Meeee (%) | Mee |
---|---|---|---|---|---|
8-Mee | M | M | M | 88 | [88] |
8-Mee | Me | Me | M | 88 | [88] |
8-Mee | M | Me | M | 88 | [88] |
MMe | Me | Me | Me | 88 | [88] |
M8 | Meeee (%) | Mee |
---|---|---|
8-Mee | 88 | [88] |
Me-Me | 88 | [88] |
Me 8888, Mee eee ee-eeeeeee eeeeeeeee e eeeeeeeee eeeeeeee eee eee eeeeeeeeeeeeeee ee eeeeeee eeeee M-eeeeeeeeeeeeeeeee ee eee eeeeee ee eeeeeeee eee eeeeeeee eee eeeeee(M) eeeeeeeeeeeeeeeee ee eeeeeeee. Me eeeeeeee, e eeeeeee ee eeeeee(MMM) eeeeeee eee eeeeee(M) eeeeeeeeeeeeeeeee (8:8) eee eeee eeeee ee ee ee eeeeeeeee eeeeeeeee eeeeeeeeeee eee eee eeee eeeeeeee (Meeeee 88). Mee eeeeeeeee eeeeeee eeeeeeee eee eeeeeeeeeeeeeee eeeeeeee 88 eee eeeeeeee ee eeeeeeeee eeeeee.[88]
Meeeee 88 Meeeee(M) Meeeeeeeeeeeeeeee Meeeeeeee Meeeeeeeeeeeeee ee Meeeeee Meeee M-Meeeeeeeeeeeeeeee[88]
M8 | M8 | M8 | Meeeeeeeeeeeeeee | ee | Meeee (%) | Mee |
---|---|---|---|---|---|---|
Me | M | Me | 88:8 | – | 88 | [88] |
M | M | Me | 8.8:8 | – | 88e | [88] |
(MM8)8 | M | – | >88:8 | 88 | [88] | |
(MM8)8M | M | >88:8 | >88:8 | 88 | [88] | |
MM8MM=MMMM8 | M | – | >88:8 | 88 | [88] |
e Meeeeeee eeeeeee eee ee 88 °M.
Meeeeeeeeeee Meeeeeeee
M-(β-Meeeeeeeeee)eeeeeeeeeeee 88; Meeeeee Meeeeeeee:[88]
M-Meeeeeeeeeeeeeeee (8.8 eeee, 8.8 eeeee) eee eeeee ee e eeee ee MeMM8 ee Me(MM8)8 (eeeeeeee ee ee eeee eeeeee ee MeMe8 eee MeMM8) (8 eee%) ee MM8Me8 (8.8 eM) eee eee eeeeeee eee eeeeeee eee 88 eee. Mee eeeeee (8.88 eeee, 8.8 eeeee) eee eeee eeeee eee eeeeeeee eee eeeeeeeee ee ee eee 88 e eeeee eeeeeeeee ee eeeee. Meeee eeeeeeeeee ee eee eeeeeeee, eee eeeeeee eee eeeeeeee eeeeeeee ee eeeee eeeeee eeeeeeeeeeeeee (eeeeeeeee eeeee/MeMMe 88:8) eee eee eeeeeee eee eeeeeeeeeeeee ee eeeeeeeeeeee.
References
[42] | Meeeeee, M. M.; Meeeee, M. M., MMM Meeee., (8888) 8, 8888, eee eeeeeeeeee eeeee eeeeeee. |
[43] | Me, M.; Mee, M.; Meeeeee, M.; Me, M., Mee. Meee., (8888) 8, 888. |
[44] | Meeeeee, M. M.; Meeeeee, M. M.; Meeeeee, M. M., Mee. Meee., (8888) 88, 888. |
[45] | Meee, M.; Mee, M.; Meeee, M.-M., Mee. Meee., (8888) 88, 8888. |