Aminochlorination

In organic synthesis, aminochlorination is a reaction that installs both a chlorine atom and an amino (or amido) group to give an 2-aminoalkyl chloride. The reaction typically is effected by combining alkene substrates with chloramines. An alternative implementation involves Pd(II)-induced nucleophilic attack of the amine on the alkene followed by oxidation by a cupric chloride.^[1]^[2]

References

^ Manzoni, Maria R.; Zabawa, Thomas P.; Kasi, Dhanalakshmi; Chemler, Sherry R. (2004). "Palladium(II)-Catalyzed Intramolecular Aminobromination and Aminochlorination of Olefins". Organometallics. 23 (23): 5618–5621. doi:10.1021/om049432z.
^ Yin, Guoyin; Mu, Xin; Liu, Guosheng (2016). "Palladium(II)-Catalyzed Oxidative Difunctionalization of Alkenes: Bond Forming at a High-Valent Palladium Center". Accounts of Chemical Research. 49 (11): 2413–2423. doi:10.1021/acs.accounts.6b00328. PMID 27739689.

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[1] Manzoni, Maria R.; Zabawa, Thomas P.; Kasi, Dhanalakshmi; Chemler, Sherry R. (2004). "Palladium(II)-Catalyzed Intramolecular Aminobromination and Aminochlorination of Olefins". Organometallics. 23 (23): 5618–5621. doi:10.1021/om049432z.

[2] Yin, Guoyin; Mu, Xin; Liu, Guosheng (2016). "Palladium(II)-Catalyzed Oxidative Difunctionalization of Alkenes: Bond Forming at a High-Valent Palladium Center". Accounts of Chemical Research. 49 (11): 2413–2423. doi:10.1021/acs.accounts.6b00328. PMID 27739689.

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