Abstract
We report the boron-catalyzed hydrophosphinylation of N-heteroaryl-substituted alkenes with secondary phosphine oxides that furnishes various phosphorus-containing N-heterocycles. This process proceeds under mild conditions and enables the introduction of a phosphorus atom into multisubstituted alkenylazaarenes. The available mechanistic data can be explained by a reaction pathway wherein the C-P bond is created by the reaction between the activated alkene (by coordination to a boron catalyst) and the phosphorus(III) nucleophile (in tautomeric equilibrium with phosphine oxide).
| Original language | English |
|---|---|
| Pages (from-to) | 15476-15487 |
| Number of pages | 12 |
| Journal | Journal of Organic Chemistry |
| Volume | 85 |
| Issue number | 23 |
| DOIs | |
| Publication status | Published - 2020 Dec 4 |
Bibliographical note
Funding Information:This work was supported by (1) the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Science, ICT & Future Planning (2018R1C1B6005712), (2) the Yonsei University Future-leading Research Initiative of 2018 (22-0055), and (3) the POSCO Cheongam Foundation (fellowship to S.Y.L.). The authors acknowledge Prof. Moon-Gun Choi (Yonsei University) for assistance on X-ray crystallographic analysis and the Pohang Accelerator Laboratory (PAL) for beamline use (2020-2nd-2D-044). S.Y.L. thanks Dr. Taegyo Lee (Pfizer) and Prof. Seung Hwan Cho (POSTECH) for helpful discussions.
Publisher Copyright:
© 2020 American Chemical Society. All rights reserved.
All Science Journal Classification (ASJC) codes
- Organic Chemistry