Azaphosphinines and their derivatives
Six-membered heterocycles containing one phosphorus and one nitrogen atom, known as azaphosphinines, have existed in the shadows of their single heteroatom-containing analogues for almost 150 years. Despite this, recent chemistry has seen a rapid increase in publications concerning this uncommon sca...
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| Published in | Chemical Society reviews Vol. 52; no. 24; pp. 8599 - 8634 |
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| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
England
Royal Society of Chemistry
11.12.2023
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| Subjects | |
| Online Access | Get full text |
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| Summary: | Six-membered heterocycles containing one phosphorus and one nitrogen atom, known as azaphosphinines, have existed in the shadows of their single heteroatom-containing analogues for almost 150 years. Despite this, recent chemistry has seen a rapid increase in publications concerning this uncommon scaffold. Azaphosphinines exist in one of six isomers-there are three possible orientations of the pnictogen atoms and in each of these, the phosphorus is in one of two valences (P
III
vs.
P
V
). This review aims to outline and inform on the synthesis and applications of all six isomers. P
V
-oxo azaphosphinines are of particular interest to this review as many of the discussed heterocycles either form as the pentavalent species directly or oxidize to this over time. In very recent years the published applications of azaphosphinines have blossomed into subjects spanning several fields of chemistry such as asymmetric catalysis, supramolecular association, cellular imaging, and medicinal chemistry.
Azaphosphinines, six-membered heterocycles containing one phosphorus and one nitrogen atom, have emerged from the shadows of their single heteroatom-containing analogues. This review describes the synthesis and applications of these unique compounds. |
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| Bibliography: | Jeremy P. Bard is an Assistant Professor of Chemistry at Washington College. He received his BS in Chemistry from Eastern Oregon University in 2016 and his PhD in Chemistry from the University of Oregon (UO) in 2021. His doctoral work, advised by Professors Michael Haley and Darren Johnson, focused on the synthesis, characterization, and utilization of azaphosphinine derivatives, and earned him a UO Dissertation Fellowship in 2020. He was a Visiting Assistant Professor at Roanoke College for one year before moving to Washington College in Fall 2022. His research group focuses on the development and synthesis of azaphosphinine-containing FRET dyes. Darren W. Johnson is Professor of Chemistry and Director of the Materials Science Institute at the University of Oregon. He performed undergraduate research with Jonathan Sessler at UT-Austin, where he earned his BSc in Chemistry in 1996. He obtained his PhD in Ken Raymond's lab at UC-Berkeley in 2000 and was an NIH NRSA postdoctoral researcher at the Scripps Research Institute with Julius Rebek, Jr. from 2001-2003. He has been at the University of Oregon since 2003, where research in the group uses supramolecular chemistry as a tool to explore a variety of problems in self-assembly, molecule/ion recognition, and inorganic cluster synthesis. J. Nolan McNeill is a 5th year PhD candidate at the University of Oregon exploring novel azaphosphinine synthesis with Professors Michael Haley and Darren Johnson. He received his BSc in Chemistry from the University of Maryland in 2019, where he worked under the tutelage of Prof. Lyle Isaacs. His research there on cucurbiturils helped him develop a distinct interest in supramolecular association. Since coming to the University of Oregon and joining the combined Haley and Johnson labs, he has co-authored several papers analyzing the emissive and supramolecular properties of benzo[e]- and pyrido[e]-1,2λ Michael M. Haley received his Bachelor's (1987) and PhD (1991) degrees from Rice University working with Prof. Ed Billups. Haley then pursued his postdoctoral studies with Prof. Peter Vollhardt at the University of California-Berkeley from 1991 to 1993. He joined the faculty at the University of Oregon in 1993 where he is currently the Richard M. and Patricia H. Noyes Professor of Chemistry. He also served as Head of the Department from 2008 to 2014. Haley is an expert in aromatic and carbon-rich molecules. He was recognized for his innovative hydrocarbon research with the 2021 American Chemical Society George A. Olah Award in Hydrocarbon or Petroleum Chemistry. 5 azaphosphinines. ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 14 ObjectType-Review-3 content type line 23 |
| ISSN: | 0306-0012 1460-4744 1460-4744 |
| DOI: | 10.1039/d3cs00737e |