- Synthesis of Cyanamides via a One-Pot Oxidation-Cyanation of Primary and Secondary Amines
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An operationally simple oxidation-cyanation method for the synthesis of cyanamides is described. The procedure utilizes inexpensive and commercially available N-chlorosuccinimide and Zn(CN)2 as reagents to avoid direct handling of toxic cyanogen halides. It is demonstrated to be amenable for the cyanation of a variety of primary and secondary amines and aniline derivatives as well as a complex synthetic intermediate en route to verubecestat (MK-8931). Additionally, kinetic measurements and other control experiments are reported to shed light onto the mechanism of this cyanation reaction.
- Kuhl, Nadine,Raval, Saurin,Cohen, Ryan D.
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supporting information
p. 1268 - 1272
(2019/03/07)
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- A general and atom-efficient continuous-flow approach to prepare amines, amides and imines via reactive N-chloramines
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Chloramines are an important class of reagents, providing a convenient source of chlorine or electrophilic nitrogen. However, the instability of these compounds is a problem which makes their isolation and handling difficult. To overcome these hazards, a continuous-flow approach is reported which generates and immediately reacts N-chloramines directly, avoiding purification and isolation steps. 2-Chloramines were produced from the reaction of styrenes with N-alkyl-N-sulfonyl-N-chloramines, whilst N-alkyl or N,N’-dialkyl-N-chloramines reacted with anisaldehyde in the presence of t-BuO2H oxidant to afford amides. Primary and secondary imines were produced under continuous conditions from the reaction of N-chloramines with base, with one example subsequently reduced under asymmetric conditions to produce a chiral amine in 94% ee.
- Jolley, Katherine E.,Chapman, Michael R.,John Blacker
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supporting information
p. 2220 - 2228
(2018/09/04)
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- AIBN-initiated metal free amidation of aldehydes using N-chloroamines
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An efficient and environmentally benign amidation of aldehydes with N-chloroamines has been developed using AIBN as an initiator. This methodology offers a metal free and base free approach and is endowed with mild reaction conditions, high yields, and good functional group tolerance.
- Vanjari, Rajeshwer,Guntreddi, Tirumaleswararao,Singh, Krishna Nand
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supporting information
p. 351 - 356
(2014/01/06)
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- MnO2 promoted sequential C-O and C-N bond formation via C-H activation of methylarenes: A new approach to amides
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A novel and efficient approach for the synthesis of amides has been developed through manganese dioxide promoted nondirected C-H activation of methylarenes under mild reaction conditions employing N-chloroamines as effective coupling partners.
- Vanjari, Rajeshwer,Guntreddi, Tirumaleswararao,Singh, Krishna Nand
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supporting information
p. 4908 - 4911
(2013/10/08)
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- [Cp*RhCl2]2-catalyzed ortho-C-H bond amination of acetophenone o-methyloximes with primary N-chloroalkylamines: Convenient synthesis of N-alkyl-2-acylanilines
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Rh(iii)-catalyzed aromatic C-H amination of acetophenone o-methyloximes with primary N-chloroalkylamines was developed, and the arylamine products were obtained in up to 92% yield. The reaction probably involves rate-limiting electrophilic C-H bond cleavage (kH/kD = 2).
- Ng, Ka-Ho,Zhou, Zhongyuan,Yu, Wing-Yiu
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supporting information
p. 7031 - 7033
(2013/09/02)
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