Halogen-Bond-Induced Consecutive Csp3-H Aminations via Hydrogen Atom Transfer Relay Strategy
The utilization of a halogen bond in a number of chemical fields is well-known. Surprisingly, the incorporation of this useful noncovalent interaction in chemical reaction engineering is rare. We disclose here an uncommon use of halogen bonding to induce intermolecular Csp3-H amination while enabling a hydrogen atom transfer relay strategy to access privileged pyrrolidine structures directly from alkanes. Mechanistic studies support the presence of multiple halogen bond interactions at distinct reaction stages.
Atmosphere- and Temperature-Controlled Regioselective Aminobromination of Olefins
A complete switch of regioselectivity in the aminobromination of olefins is realized from delicate changes in the reaction temperature from 25 °C to 40 °C and the atmosphere from air to argon, under catalyst-free conditions. The resulting α-bromoamides ca
Yu, Wesley Zongrong,Cheng, Yi An,Wong, Ming Wah,Yeung, Ying-Yeung
p. 234 - 239
(2017/02/05)
Catalyst-free aminobromination of alkenes with N-methyl-p-toluenesulfonamide as nitrogen resource
A catalyst-free electrophilic aminobromination system was described with N-methyl-p-toluenesulfonamide (p-TsNHCH3) and N-bromosuccinimide (NBS) as nitrogen and bromine resources. The reaction can give vicinal haloamines in good yields, excellent regioselectivities, and stereoselectivities under convenient and mild condition. The existence of N-methyl group in the nitrogen resource was found to play an important role in the formation of vicinal haloamine product.