2021
DOI: 10.1021/acs.oprd.1c00165
|View full text |Cite
|
Sign up to set email alerts
|

Copper-Catalyzed, Aerobic Oxidation of Hydrazone in a Three-Phase Packed Bed Reactor

Abstract: Copper-catalyzed, aerobic hydrazone oxidation to produce synthetically useful diazo compounds is achieved in a continuous, three-phase flow reactor with complete conversion and high selectivity by adapting a previously published batch methodology to a flow system described herein and conducting a parameter space exploration to optimize the process conditions. The robust nature of the process is demonstrated, with complete hydrazone conversion and a 90% steady-state diazo compound selectivity maintained over 11… Show more

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...

Citation Types

0
10
0

Year Published

2021
2021
2024
2024

Publication Types

Select...
7

Relationship

1
6

Authors

Journals

citations
Cited by 11 publications
(10 citation statements)
references
References 83 publications
0
10
0
Order By: Relevance
“…3C): p bond cycloaddition (54 to 56) and s bond insertion (57 and 58). We expect this formaldehyde-based approach to provide a safer alternative to conventional diazomethane reactivity and to complement modern methods that entail in situ generation (7)(8)(9).…”
mentioning
confidence: 99%
See 1 more Smart Citation
“…3C): p bond cycloaddition (54 to 56) and s bond insertion (57 and 58). We expect this formaldehyde-based approach to provide a safer alternative to conventional diazomethane reactivity and to complement modern methods that entail in situ generation (7)(8)(9).…”
mentioning
confidence: 99%
“…Given the strong entropic and enthalpic driving forces inherent in the release of N 2 from these reagents, strict precautions are necessary to prevent explosive, uncontrolled chain reactions ( 6 ). Strategies to address this underlying safety issue include flow chemistry and in situ diazotization ( 7 9 ). Carbonyl and arene stabilizing groups are also frequently used ( 10 ), which influence carbene polarity and selectivity ( 11 , 12 ).…”
mentioning
confidence: 99%
“…35 Having established the batch reaction, we are now developing flow methods for the synthesis of the aryldiazoacetates. We are interested in two distinct applications, a process potentially amenable for industrial scale 36 and a technically simpler labtop procedure.…”
mentioning
confidence: 99%
“…The process avoids the engineering challenges of regeneration of the copper(II) salt using air as the terminal oxidant, although a process using copper in catalytic amounts may be required for a practical industrial-scale process. 36…”
mentioning
confidence: 99%
See 1 more Smart Citation