Abstract
In recent years, photoredox catalysis has appeared as a new paradigm for forging a wide range of chemical bonds under mild conditions using abundant reagents. This approach allows many organic transformations through the generation of various radical species, enabling the valorization of non-traditional partners. A continuing interest has been devoted to the discovery of novel radical-generating procedures. Over the last ten years, strategies using rare-earth complexes as either redox-active centers or as redox-neutral Lewis acids have emerged. This review provides an overview of the recent accomplishments made in this field. It especially aims to demonstrate the utility of rare-earth complexes for ensuring photocatalytic transformations and to inspire future developments.
Keywords: Photocatalysis, radicals, rare-earth metals, lanthanides, Lewis acid, redox chemistry, photocyclization.
Graphical Abstract
[http://dx.doi.org/10.1021/acs.chemrev.6b00057] [PMID: 27285582]
[http://dx.doi.org/10.1021/acs.joc.6b01449] [PMID: 27477076]
[http://dx.doi.org/10.1021/cr300503r] [PMID: 23509883]
[http://dx.doi.org/10.1039/B913880N] [PMID: 20532341]
[http://dx.doi.org/10.1021/acscatal.7b01385]
[http://dx.doi.org/10.3390/molecules25173892] [PMID: 32858962]
[http://dx.doi.org/10.1021/acs.accounts.8b00336] [PMID: 30335356]
[http://dx.doi.org/10.1016/j.ccr.2018.03.004]
[http://dx.doi.org/10.1021/acs.accounts.6b00280] [PMID: 27505691]
[http://dx.doi.org/10.1002/ajoc.201600576]
[http://dx.doi.org/10.1021/cr400685r] [PMID: 24758360]
[http://dx.doi.org/10.1021/cr068408n] [PMID: 17432919]
[http://dx.doi.org/10.1021/cr010289i] [PMID: 12059268]
[http://dx.doi.org/10.1055/s-0036-1588321]
[http://dx.doi.org/10.3184/003685005783238435] [PMID: 16749431]
[http://dx.doi.org/10.1016/j.tet.2003.08.070]
[http://dx.doi.org/10.1021/ja963117p]
[http://dx.doi.org/10.1021/jo980119e]
[http://dx.doi.org/10.1246/cl.1985.893]
[http://dx.doi.org/10.1246/bcsj.59.1195]
[http://dx.doi.org/10.1039/c39850001481]
[http://dx.doi.org/10.1246/cl.1988.1497]
[http://dx.doi.org/10.1002/anie.201609035] [PMID: 27862775]
[http://dx.doi.org/10.31635/ccschem.020.201900076]
[http://dx.doi.org/10.1021/jacs.8b08781] [PMID: 30289250]
[http://dx.doi.org/10.1016/j.chempr.2019.11.009]
[http://dx.doi.org/10.1002/anie.202012720] [PMID: 33259085]
[http://dx.doi.org/10.1021/jacs.1c00618] [PMID: 33756079]
[http://dx.doi.org/10.1021/jacs.9b05932] [PMID: 31244192]
[http://dx.doi.org/10.1021/jacs.7b13131] [PMID: 29381061]
[http://dx.doi.org/10.1126/science.aat9750] [PMID: 30049785]
[http://dx.doi.org/10.1021/jacs.0c00212] [PMID: 32181657]
[http://dx.doi.org/10.1126/science.abd8408] [PMID: 34016778]
[http://dx.doi.org/10.1021/ja01026a022]
[http://dx.doi.org/10.1039/C9CC00492K] [PMID: 30829348]
[http://dx.doi.org/10.1039/C9OB02676B] [PMID: 31939464]
[http://dx.doi.org/10.1021/jacs.9b12918] [PMID: 32109060]
[http://dx.doi.org/10.1039/D0SC04542J] [PMID: 33384861]
[http://dx.doi.org/10.1039/C9CC00035F] [PMID: 30766977]
[http://dx.doi.org/10.1039/C9CC04785A] [PMID: 31347637]
[http://dx.doi.org/10.1016/j.tetlet.2018.04.060]
[http://dx.doi.org/10.1016/j.electacta.2010.02.099]
[http://dx.doi.org/10.1002/anie.202007668] [PMID: 32677341]
[http://dx.doi.org/10.1039/D0SC00712A] [PMID: 32864080]
[http://dx.doi.org/10.1038/s41570-017-0052]
[http://dx.doi.org/10.1007/s41061-016-0037-z] [PMID: 27573391]
[http://dx.doi.org/10.1021/acscatal.7b00094] [PMID: 28413692]
[http://dx.doi.org/10.1002/chem.202003974] [PMID: 33111994]
[http://dx.doi.org/10.1126/science.1253647] [PMID: 24903560]
[http://dx.doi.org/10.1126/science.1255525] [PMID: 24903563]
[http://dx.doi.org/10.1002/anie.201504963] [PMID: 26216069]
[http://dx.doi.org/10.1002/anie.201606513] [PMID: 27709775]
[http://dx.doi.org/10.1002/anie.201709571] [PMID: 28984403]
[http://dx.doi.org/10.1021/jacs.8b07405] [PMID: 30184423]
[http://dx.doi.org/10.1038/s41586-018-0366-x] [PMID: 30068953]
[http://dx.doi.org/10.1039/D0SC01471K] [PMID: 34122946]
[http://dx.doi.org/10.1038/s41467-018-06904-9] [PMID: 30382103]
[http://dx.doi.org/10.1021/jacs.6b09533] [PMID: 27718570]
[http://dx.doi.org/10.1021/acscatal.9b00405]
[http://dx.doi.org/10.1021/jacs.5b07678] [PMID: 26322524]
[http://dx.doi.org/10.1021/acs.joc.5b00794] [PMID: 26030387]
[http://dx.doi.org/10.1021/ja408971t] [PMID: 24074152]
[http://dx.doi.org/10.1021/jacs.8b02650] [PMID: 29754491]
[http://dx.doi.org/10.1021/jacs.8b02834] [PMID: 29664294]
[http://dx.doi.org/10.1038/nature19056] [PMID: 27535536]
[http://dx.doi.org/10.1039/c39910000757]
[http://dx.doi.org/10.1016/S0040-4039(97)10409-9]
[http://dx.doi.org/10.1039/C7SC02479G] [PMID: 29675173]
[http://dx.doi.org/10.1021/jacs.5b05411] [PMID: 26151154]
[http://dx.doi.org/10.1021/jacs.6b02248] [PMID: 27058605]
[http://dx.doi.org/10.1002/anie.201804022] [PMID: 29752881]
[http://dx.doi.org/10.1002/chem.201701665] [PMID: 28429580]
[http://dx.doi.org/10.1021/jacs.5b02506] [PMID: 25853298]
[http://dx.doi.org/10.1039/C8CC01737A] [PMID: 29662990]
[http://dx.doi.org/10.1021/acs.inorgchem.0c01516] [PMID: 32618468]
[http://dx.doi.org/10.1021/jacs.6b05712] [PMID: 27936638]
[http://dx.doi.org/10.1021/jacs.7b13339] [PMID: 29359933]
[http://dx.doi.org/10.1021/acs.chemrev.0c01236] [PMID: 33596057]
[http://dx.doi.org/10.1039/D1OB00323B] [PMID: 33913460]
[http://dx.doi.org/10.1021/acscatal.6b01452]
[http://dx.doi.org/10.1021/acs.chemrev.6b00018] [PMID: 27109441]
[http://dx.doi.org/10.1002/chem.201304823] [PMID: 24596102]
[http://dx.doi.org/10.1039/D1RA00925G]
[http://dx.doi.org/10.1021/ja00297a005]
[http://dx.doi.org/10.1021/jp012709d]
[http://dx.doi.org/10.1039/C5CC00178A] [PMID: 25647055]
[http://dx.doi.org/10.1021/ja031649h] [PMID: 15198606]
[http://dx.doi.org/10.1002/chem.201601517] [PMID: 27249665]
[http://dx.doi.org/10.1002/ejoc.202100518] [PMID: 34248414]
[http://dx.doi.org/10.1002/cctc.202001195]
[http://dx.doi.org/10.1021/acs.chemrev.5b00723] [PMID: 27018601]
[http://dx.doi.org/10.1021/jacs.8b01011] [PMID: 29458250]
[http://dx.doi.org/10.1021/acs.accounts.6b00586] [PMID: 28128920]
[http://dx.doi.org/10.1002/chem.201804600] [PMID: 30341931]
[http://dx.doi.org/10.1002/anie.202001200] [PMID: 32056352]
[http://dx.doi.org/10.1126/science.1251511] [PMID: 24763585]
[http://dx.doi.org/10.1126/science.aai8228] [PMID: 27980203]
[http://dx.doi.org/10.1002/anie.201706975] [PMID: 28776908]
[http://dx.doi.org/10.1021/acscatal.7b04032]
[http://dx.doi.org/10.1021/ja805387f] [PMID: 18767798]
[http://dx.doi.org/10.1021/ja107849y] [PMID: 21214249]
[http://dx.doi.org/10.1021/jacs.6b01728] [PMID: 27015009]
[http://dx.doi.org/10.1021/jo300796j] [PMID: 22731518]
[http://dx.doi.org/10.1038/s41467-017-02698-4] [PMID: 29379007]
[http://dx.doi.org/10.1021/ja512746q] [PMID: 25668687]
[http://dx.doi.org/10.1021/jacs.7b01373] [PMID: 28358497]
[http://dx.doi.org/10.1021/acs.orglett.8b02442] [PMID: 30188722]
[http://dx.doi.org/10.1021/acs.orglett.8b02893] [PMID: 30346177]
[http://dx.doi.org/10.1039/C8SC02106F] [PMID: 30310630]
[http://dx.doi.org/10.1021/acscatal.0c03776]
[http://dx.doi.org/10.1021/acs.orglett.0c02314] [PMID: 32806138]
[http://dx.doi.org/10.1039/D0CC05167E] [PMID: 32869792]