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- Title
Photochemical Generation of Chiral N,B,X‐Heterocycles by Heteroaromatic C−X Bond Scission (X=S, O) and Boron Insertion.
- Authors
Mellerup, Soren K.; Li, Cally; Radtke, Julian; Wang, Xiang; Li, Quan‐Song; Wang, Suning
- Abstract
Abstract: Chiral organoboron compounds with a chelate backbone and mesityl/heterocycle substituents (thienyl, furyl, and derivatives thereof) undergo a quantitative phototransformation that yields rare, chiral N,B,X‐containing heterocycles, such as base‐stabilized 1,2‐thiaborinines and 1,2‐oxaborinines. Boriranes were observed as intermediates in some of these transformations. The oxaborinines display further reactivity, generating 4a,12b‐dihydrobenzo[h][1,2]oxaborinino[4,3‐f]quinolines through a sequential conrotatory electrocyclization and a [1,5]‐H shift. The N,B,X‐containing heterocycles display strong blue‐green to orange‐red emission in the solid state. Combined DFT//CASP2T calculations suggest that a common biradical intermediate is responsible for the formation of these compounds as well as their interconversion.
- Subjects
HETEROCYCLIC compounds; BORON compounds; THIENYL compounds; STABILIZING agents; REACTIVITY (Chemistry); RING formation (Chemistry)
- Publication
Angewandte Chemie, 2018, Vol 130, Issue 31, p9782
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201803760