Deaminative Chlorination of Aminoheterocycles

A Large Step Forward For Late Stage Functionalization

Topic Area
Synthetic chemistry (non-biological)
Article Type
Primary Research

Logic / Design

Point of Paper
Very clear
Main Conclusions
Supported by evidence presented


Key Procedures
Able to reproduce all
# Procedures Attempted
1 to 3
Of Attempted, # Reproduced


Replicated Methods Exactly:
Minor Changes
Reviewer Improvements
Slight improvements


Applicability to Other Fields
Probably not
Use in Own Work
Yes, and it was useful


Overall Clarity
Exceptionally clear & well-written


Signifcantly advances the field


Funding Sources
Unable to comment
Conflicts of Interest
Not aware of any


Safety Concerns
None or clearly mentioned
All commercially available


A simple but effective replacement for the Sandmeyer reaction. The avoidance of diazonium salts, copper, and the general functional group tolerability make this deamination reaction extremely valuable for late stage functionalization strategies. Initial testing in-house would suggest that the observations are reproducible and scalable on complex substrates. This is a valuable addition to the chemistry toolbox, and complimentary to other displacement approaches as dictated by substructure tolerability and building block availability.

The only criticism would be better reporting of reaction temperatures in the figures per each substrate (they are reported in the SI) -- naturally the lower temperatures are more desirable. Overall a great paper with consise results and honest reporting of yields and limitations.

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