Abstract
Organoselenium chemistry has emerged as a distinctive area of research with tremendous utility in the synthesis of biologically and pharmaceutically active molecules. Significant synthetic approaches have been made for the construction of C-Se bonds, which are useful in other organic transformations. This review focuses on the versatility of transition metal-mediated selenylation reactions, providing insights into various synthetic pathways and mechanistic details. Furthermore, this review aims to offer a broad perspective for designing efficient and novel catalysts to incorporate organoselenium moiety into the inert C-H bonds.
Keywords: Selenylation, organoselenium, diselenides, C-H functionalization, transition metals, C-Se bonds.
Graphical Abstract
[http://dx.doi.org/10.1016/j.tetlet.2015.04.045]
[http://dx.doi.org/10.1002/anie.200903893] [PMID: 19802863]
[http://dx.doi.org/10.1039/c3cc43950j] [PMID: 23903206]
[http://dx.doi.org/10.1039/C5QO00179J]
[http://dx.doi.org/10.1021/ja311202e] [PMID: 23312005]
[http://dx.doi.org/10.1021/ol202800k] [PMID: 22085140]
[http://dx.doi.org/10.1021/acscatal.7b02729]
[http://dx.doi.org/10.1038/s41467-018-02955-0] [PMID: 29410415]
[http://dx.doi.org/10.1002/anie.201601713] [PMID: 27027644]
[http://dx.doi.org/10.1038/nchem.2109] [PMID: 25411883]
[http://dx.doi.org/10.1007/s00204-011-0720-3] [PMID: 21720966]
[http://dx.doi.org/10.1002/chem.201803776] [PMID: 30225936]
[http://dx.doi.org/10.1211/jpp.61.05.0011] [PMID: 19406001]
[http://dx.doi.org/10.1186/s12866-016-0837-x] [PMID: 27654924]
[http://dx.doi.org/10.3390/molecules23030628] [PMID: 29534447]
[http://dx.doi.org/10.1161/01.STR.29.1.12] [PMID: 9445321]
[http://dx.doi.org/10.1021/cb400485k] [PMID: 24134695]
[http://dx.doi.org/10.1038/s41586-020-2223-y] [PMID: 32272481]
[http://dx.doi.org/10.1002/ejoc.201403534]
[http://dx.doi.org/10.1002/adsc.201401159]
[http://dx.doi.org/10.1002/ejoc.201701205]
[http://dx.doi.org/10.1039/b914533h] [PMID: 19907775]
[http://dx.doi.org/10.1039/C7GC02803B]
[http://dx.doi.org/10.1039/c1gc15725f]
[http://dx.doi.org/10.1016/j.cclet.2017.06.023]
[http://dx.doi.org/10.1246/bcsj.64.416]
[http://dx.doi.org/10.1002/ejoc.201900992]
[http://dx.doi.org/10.1002/anie.201509164] [PMID: 26662619]
[http://dx.doi.org/10.1002/adsc.200900095]
[http://dx.doi.org/10.1021/acs.joc.6b02108] [PMID: 27731643]
[http://dx.doi.org/10.1016/j.tetlet.2009.09.052]
[http://dx.doi.org/10.1039/c2gc16427b]
[http://dx.doi.org/10.1021/acs.orglett.5b02511] [PMID: 26562356]
[http://dx.doi.org/10.1021/acs.orglett.6b01420] [PMID: 27309343]
[http://dx.doi.org/10.1021/ol802060f] [PMID: 18826235]
[http://dx.doi.org/10.1002/slct.201702371]
[http://dx.doi.org/10.1039/C8QO00840J]
[http://dx.doi.org/10.1002/slct.201702623]
[http://dx.doi.org/10.1002/jlac.18671430315]
[http://dx.doi.org/10.1021/acs.joc.6b02388] [PMID: 27966941]
[http://dx.doi.org/10.1021/acs.joc.6b02865] [PMID: 28220698]
[http://dx.doi.org/10.1021/jo062131+] [PMID: 17288374]
[http://dx.doi.org/10.1016/j.tet.2013.04.124]
[http://dx.doi.org/10.1002/asia.201300882] [PMID: 24347073]
[http://dx.doi.org/10.1021/acscentsci.6b00272] [PMID: 27981231]
[http://dx.doi.org/10.1002/adsc.201600759]
[http://dx.doi.org/10.1021/acs.joc.7b00050] [PMID: 28195467]
[http://dx.doi.org/10.1021/acs.joc.5b01448] [PMID: 26158240]
[http://dx.doi.org/10.1246/cl.2011.1254]
[http://dx.doi.org/10.1080/00397911.2011.584262]
[http://dx.doi.org/10.1039/C6OB00209A] [PMID: 27099126]
[http://dx.doi.org/10.1021/ol503231p] [PMID: 25515149]
[http://dx.doi.org/10.1021/acs.joc.5b01943] [PMID: 26686383]
[http://dx.doi.org/10.1021/acscatal.7b01645]
[http://dx.doi.org/10.1002/adsc.201800755]
[http://dx.doi.org/10.1021/acs.joc.6b00634] [PMID: 27104776]
[http://dx.doi.org/10.1021/acs.orglett.7b00674] [PMID: 28358203]
[http://dx.doi.org/10.1021/acs.orglett.7b00996] [PMID: 28429594]
[http://dx.doi.org/10.1039/C6CS00107F] [PMID: 27056573]
[http://dx.doi.org/10.1039/C4OB01992J] [PMID: 25333205]
[http://dx.doi.org/10.1021/acs.joc.8b01361] [PMID: 29993245]
[http://dx.doi.org/10.1055/s-1995-4978]
[http://dx.doi.org/10.1021/ja039107n] [PMID: 14759185]
[http://dx.doi.org/10.1039/c0cy00076k]
[http://dx.doi.org/10.1021/jo502402d] [PMID: 25437148]
[http://dx.doi.org/10.1002/anie.201411997] [PMID: 25783208]
[http://dx.doi.org/10.1002/ajoc.201500192]
[http://dx.doi.org/10.1016/j.tet.2018.09.048]
[http://dx.doi.org/10.1038/nature13274] [PMID: 24828188]
[http://dx.doi.org/10.1246/cl.150024]
[http://dx.doi.org/10.1021/acs.orglett.5b00337] [PMID: 25714854]
[http://dx.doi.org/10.1021/acs.joc.6b01702] [PMID: 27626937]
[http://dx.doi.org/10.1002/chem.201603092] [PMID: 27501081]
[http://dx.doi.org/10.1021/acs.orglett.7b00116] [PMID: 28211695]
[http://dx.doi.org/10.1016/j.tet.2018.09.037]
[http://dx.doi.org/10.1021/acs.joc.6b01715] [PMID: 27661444]
[http://dx.doi.org/10.1039/C7OB00668C] [PMID: 28530762]