Dissecting the Flash Chemistry of Electrogenerated Reactive Intermediates by Microdroplet Fusion Mass Spectrometry
A novel mass spectrometric method for probing the flash chemistry of electrogenerated reactive intermediates was developed based on rapid collision mixing of electrosprayed microdroplets by using a theta‐glass capillary. The two individual microchannels of the theta‐glass capillary are asymmetricall...
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| Published in | Angewandte Chemie International Edition Vol. 60; no. 34; pp. 18494 - 18498 |
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| Main Authors | , , , , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Weinheim
Wiley Subscription Services, Inc
16.08.2021
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| Edition | International ed. in English |
| Subjects | |
| Online Access | Get full text |
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| Abstract | A novel mass spectrometric method for probing the flash chemistry of electrogenerated reactive intermediates was developed based on rapid collision mixing of electrosprayed microdroplets by using a theta‐glass capillary. The two individual microchannels of the theta‐glass capillary are asymmetrically or symmetrically fabricated with a carbon bipolar electrode to produce intermediates in situ. Microdroplets containing the newly formed intermediates collide with those of the invoked reactants at sub‐10 microsecond level, making it a powerful tool for exploring their ultrafast initial transformations. As a proof‐of‐concept, we present the identification of the key radical cation intermediate in the oxidative dimerization of 8‐methyl‐1,2,3,4‐tetrahydroquinoline and also the first disclosure of previously hidden nitrenium ion involved reaction pathway in the C−H/N−H cross‐coupling between N,N′‐dimethylaniline and phenothiazine.
Microreactor on the fly: A special microreactor that permits mass spectrometric probing the flash chemistry of electrogenerated reactive intermediates was demonstrated based on collision mixing of electrosprayed microdroplets, which employed a theta‐glass capillary integrated with carbon bipolar electrodes to produce short‐lived intermediates in situ. |
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| AbstractList | A novel mass spectrometric method for probing the flash chemistry of electrogenerated reactive intermediates was developed based on rapid collision mixing of electrosprayed microdroplets by using a theta‐glass capillary. The two individual microchannels of the theta‐glass capillary are asymmetrically or symmetrically fabricated with a carbon bipolar electrode to produce intermediates in situ. Microdroplets containing the newly formed intermediates collide with those of the invoked reactants at sub‐10 microsecond level, making it a powerful tool for exploring their ultrafast initial transformations. As a proof‐of‐concept, we present the identification of the key radical cation intermediate in the oxidative dimerization of 8‐methyl‐1,2,3,4‐tetrahydroquinoline and also the first disclosure of previously hidden nitrenium ion involved reaction pathway in the C−H/N−H cross‐coupling between N,N′‐dimethylaniline and phenothiazine. A novel mass spectrometric method for probing the flash chemistry of electrogenerated reactive intermediates was developed based on rapid collision mixing of electrosprayed microdroplets by using a theta‐glass capillary. The two individual microchannels of the theta‐glass capillary are asymmetrically or symmetrically fabricated with a carbon bipolar electrode to produce intermediates in situ. Microdroplets containing the newly formed intermediates collide with those of the invoked reactants at sub‐10 microsecond level, making it a powerful tool for exploring their ultrafast initial transformations. As a proof‐of‐concept, we present the identification of the key radical cation intermediate in the oxidative dimerization of 8‐methyl‐1,2,3,4‐tetrahydroquinoline and also the first disclosure of previously hidden nitrenium ion involved reaction pathway in the C−H/N−H cross‐coupling between N,N′‐dimethylaniline and phenothiazine. Microreactor on the fly: A special microreactor that permits mass spectrometric probing the flash chemistry of electrogenerated reactive intermediates was demonstrated based on collision mixing of electrosprayed microdroplets, which employed a theta‐glass capillary integrated with carbon bipolar electrodes to produce short‐lived intermediates in situ. A novel mass spectrometric method for probing the flash chemistry of electrogenerated reactive intermediates was developed based on rapid collision mixing of electrosprayed microdroplets by using a theta-glass capillary. The two individual microchannels of the theta-glass capillary are asymmetrically or symmetrically fabricated with a carbon bipolar electrode to produce intermediates in situ. Microdroplets containing the newly formed intermediates collide with those of the invoked reactants at sub-10 microsecond level, making it a powerful tool for exploring their ultrafast initial transformations. As a proof-of-concept, we present the identification of the key radical cation intermediate in the oxidative dimerization of 8-methyl-1,2,3,4-tetrahydroquinoline and also the first disclosure of previously hidden nitrenium ion involved reaction pathway in the C-H/N-H cross-coupling between N,N'-dimethylaniline and phenothiazine.A novel mass spectrometric method for probing the flash chemistry of electrogenerated reactive intermediates was developed based on rapid collision mixing of electrosprayed microdroplets by using a theta-glass capillary. The two individual microchannels of the theta-glass capillary are asymmetrically or symmetrically fabricated with a carbon bipolar electrode to produce intermediates in situ. Microdroplets containing the newly formed intermediates collide with those of the invoked reactants at sub-10 microsecond level, making it a powerful tool for exploring their ultrafast initial transformations. As a proof-of-concept, we present the identification of the key radical cation intermediate in the oxidative dimerization of 8-methyl-1,2,3,4-tetrahydroquinoline and also the first disclosure of previously hidden nitrenium ion involved reaction pathway in the C-H/N-H cross-coupling between N,N'-dimethylaniline and phenothiazine. |
| Author | Hu, Jun Gao, Hang Wang, Ting Zhang, Wen‐Jun Xia, Xing‐Hua Yu, Qiao Zhang, Nan Chen, Yun Hao, Han Chen, Hong‐Yuan Xu, Jing‐Juan |
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| Snippet | A novel mass spectrometric method for probing the flash chemistry of electrogenerated reactive intermediates was developed based on rapid collision mixing of... |
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| StartPage | 18494 |
| SubjectTerms | Cross coupling Dimerization electrospray ionization Intermediates Mass spectrometry Mass spectroscopy Microchannels microdroplet reaction Phenothiazine reactive radical intermediate |
| Title | Dissecting the Flash Chemistry of Electrogenerated Reactive Intermediates by Microdroplet Fusion Mass Spectrometry |
| URI | https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fanie.202106945 https://www.proquest.com/docview/2559384305 https://www.proquest.com/docview/2541323204 |
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