Safe and Efficient Tetrazole Synthesis in a Continuous-Flow Microreactor

Safer flow: The synthesis of 5‐substituted tetrazoles in flow (see scheme) is safe, efficient, scalable, requires no metal promoter, and uses a near‐equimolar amount of NaN3, yet nonetheless displays a broad substrate scope. The hazards associated with HN3 are essentially eliminated, shock‐sensitive...

Full description

Saved in:
Bibliographic Details
Published inAngewandte Chemie International Edition Vol. 50; no. 15; pp. 3525 - 3528
Main Authors Palde, Prakash B., Jamison, Timothy F.
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 04.04.2011
WILEY‐VCH Verlag
Wiley
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
azides
Bioreactors
Chemistry
Chemistry, Multidisciplinary
continuous-flow synthesis
Microchemistry
microreactors
Physical Sciences
Science & Technology
synthetic methods
tetrazoles
Tetrazoles - chemical synthesis
Tetrazoles - chemistry
5-SUBSTITUTED 1H-TETRAZOLES
HYDRAZOIC ACID
REACTORS
continuous-flow synthesis
CONVERSION
CATALYZED SYNTHESIS
azides
AZIDE
tetrazoles
NITRILES
microreactors
CHEMISTRY
synthetic methods
TOOL
Online AccessGet full text

Cover

More Information
Summary:Safer flow: The synthesis of 5‐substituted tetrazoles in flow (see scheme) is safe, efficient, scalable, requires no metal promoter, and uses a near‐equimolar amount of NaN3, yet nonetheless displays a broad substrate scope. The hazards associated with HN3 are essentially eliminated, shock‐sensitive metal azides such as Zn(N3)2 are avoided, and residual NaN3 is quenched in‐line with NaNO2.
Bibliography:We are grateful to the Novartis-MIT Center for Continuous Manufacturing for financial support and to several colleagues at MIT (Stephen L. Buchwald, Klavs F. Jensen, and their co-workers) and Novartis (Gerhard Penn, Berthold Schenkel, Oljan Repic, Thierry Schlama, Mike Girgis, Lukas Padeste, and Felix Kollmer) for insightful discussions.
istex:502F09F6AA8C3A256C54309A4BEA11B17A48458F
ark:/67375/WNG-3M91Q3BQ-4
ArticleID:ANIE201006272
We are grateful to the Novartis‐MIT Center for Continuous Manufacturing for financial support and to several colleagues at MIT (Stephen L. Buchwald, Klavs F. Jensen, and their co‐workers) and Novartis (Gerhard Penn, Berthold Schenkel, Oljan Repic, Thierry Schlama, Mike Girgis, Lukas Padeste, and Felix Kollmer) for insightful discussions.
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201006272