Convenient access to π-conjugated 1,3-azaphospholes from alkynes via [3 + 2]-cycloaddition and reductive aromatization
Research output: Contribution to journal › Research article › Contributed › peer-review
Contributors
Abstract
When incorporated into π-conjugated systems, phosphorus-based heterocycles have gained significant attention due to their unique chemical and physical properties. However, their syntheses remain challenging. Herein, we describe a novel [3+2]-cycloaddition between 1,3-dipolar triflatophosphanes and alkynes, affording azaphospholium salts. These salts can be reduced to generate the targeted 1,3-azaphospholes and an NHC (N-heterocyclic carbene) byproduct. The reaction is high-yielding, scalable, and can tolerate a wide array of sterically and electronically diverse alkynes, leading to a library of 1,3-azaphospholes (19 examples, up to 99% yield). As a broad range of structural modifications is covered, information on structure-property relationships is extracted from joint experimental and theoretical analysis, revealing efficient strategies for further optimizations. Their high thermal stability and tunable electronic structure render them a promising platform for future applications.
Details
Original language | English |
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Pages (from-to) | 644-659 |
Number of pages | 16 |
Journal | Chem |
Volume | 10 |
Issue number | 2 |
Publication status | Published - 8 Feb 2024 |
Peer-reviewed | Yes |
External IDs
ORCID | /0000-0002-4112-6991/work/163295279 |
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ORCID | /0000-0001-7323-7816/work/163295543 |
Keywords
ASJC Scopus subject areas
Keywords
- cycloaddition, dipolar, phospholes, phosphorus, photophysics, polyaromatic compounds, SDG9: Industry, innovation, and infrastructure