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Generation and Reactions of o-Bromophenyllithium without Benzyne Formation Using a Microreactor
Abstract
Microflow systems were found to serve as powerful tools for mechanistic studies on reactions involving highly unstable intermediates such as o -bromophenyllithium, which is known to decompose to benzyne very quickly even at −78 °C. Precise residence time control and precise temperature control of microsystems are responsible. Based on the information thus obtained, the Br−Li exchange reaction of o -dibromobenzene followed by reactions with electrophiles without benzyne formation was achieved using a microflow system. Sequential use of two bromine atoms in o -dibromobenzene with Br−Li exchange reactions followed by the reactions with electrophiles using the microsystem consisting of four micromixers and four microtube reactors was also accomplished.
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Cited by
Taming hazardous chemistry by continuous flow technology
Movsisyan, M., Delbeke, E. I. P., Berton, J. K. E. T., Battilocchio, C., Ley, S. V., & Stevens, C. V. (2016) · Chemical Society Reviews · doi:10.1039/c5cs00902b · Cited by 692
Flash Chemistry: Fast Chemical Synthesis by Using Microreactors
Yoshida, J., Nagaki, A., & Yamada, T. (2008) · Chemistry – A European Journal · doi:10.1002/chem.200800582 · Cited by 537
Self-citationMicrochemical systems for continuous-flow synthesis
Hartman, R. L., & Jensen, K. F. (2009) · Lab on a Chip · doi:10.1039/b906343a · Cited by 508
Flash chemistry: flow chemistry that cannot be done in batch
Yoshida, J.-I., Takahashi, Y., & Nagaki, A. (2013) · Chem. Commun. · doi:10.1039/c3cc44709j · Cited by 450
Self-citationFlash chemistry: flow microreactor synthesis based on high‐resolution reaction time control
Yoshida, J. (2010) · The Chemical Record · doi:10.1002/tcr.201000020 · Cited by 277
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Metadata
- Authors
- Usutani, H., Tomida, Y., Nagaki, A., Okamoto, H., Nokami, T., & Yoshida, J.-I.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2007-02-27
- Volume
- 129
- Issue
- 11
- Pages
- 3046-3047
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2020338350
- Cited by
- 267
- References
- 0
- FWCI
- 17.14
- Type
- journal article
- Language
- en
- Open access
- closed
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- Usutani, H., Tomida, Y., Nagaki, A., Okamoto, H., Nokami, T., & Yoshida, J.-I. (2007). Generation and Reactions of o-Bromophenyllithium without Benzyne Formation Using a Microreactor. Journal of the American Chemical Society. https://doi.org/10.1021/ja068330s
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