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organocerium chemistry wikipedia jump to content main menu main menu move to sidebar hide navigation main page contents current events random article about wikipedia contact us contribute help learn to edit community portal recent changes upload file special pages search search appearance donate create account log in personal tools donate create account log in contents move to sidebar hide top 1 alkyl derivatives 2 cyclopentadienyl derivatives 3 applications to organic synthesis 4 reactions 5 see also 6 references toggle the table of contents organocerium chemistry 5 languages català čeština עברית nederlands српски srpski edit links article talk english read edit view history tools tools move to sidebar hide actions read edit view history general what links here related changes upload file permanent link page information cite this page get shortened url switch to legacy parser print export download as pdf printable version in other projects wikidata item appearance move to sidebar hide from wikipedia the free encyclopedia redirected from organocerium science of specific organometallic compounds structure of c 5 ch 3 4 h 3 ce color code green ce gray c white h organocerium chemistry is the science of organometallic compounds that contain one or more chemical bond between carbon and cerium these compounds comprise a subset of the organolanthanides most organocerium compounds feature ce iii but some ce iv derivatives are known alkyl derivatives edit structure of ce ch 3 6 li tmeda 3 where tmeda is ch 3 2 nch 2 ch 2 n ch 3 2 simple alkylcerium reagents are well known one example is li tmeda 3 ce ch 3 6 1 although they are described as rcecl 2 their structures are far more complex 2 furthermore the solvent seems to alter the solution structure of the complex with differences noted between reagents prepared in diethyl ether and tetrahydrofuran there is evidence that the parent chloride forms a polymeric species in thf solution of the form ce μ cl 2 h 2 o thf 2 n but whether this type of polymer exists once the organometallic reagent is formed is unknown 3 cyclopentadienyl derivatives edit cyclopentadienyl derivatives of ce are particularly well characterized hundreds have been examined by x ray crystallography the depicted c 5 ch 3 4 h 3 ce is one of many 4 some of the best characterized organocerium iv compounds feature cyclopentadienyl ligands e g ce c 5 h 5 3 cl 5 applications to organic synthesis edit as reagents in organic chemistry organocerium compounds are typically prepared in situ by treatment of cerium trichloride with organolithium or grignard reagent reagents are derived from alkyl alkynyl and alkenyl organometallic reagents as well as enolates have been described 6 2 7 3 8 the most common cerium source for this purpose is cerium iii chloride 9 which can be obtained in anhydrous form via dehydration of the commercially available hepta hydrate precomplexation with tetrahydrofuran is important for the success of the transmetallation with most procedures involving vigorous stirring for a period of no less than 2 hours 2 the structures depicted as below for organocerium reagent however are highly simplified examples of various organocerium reagents previously reported these reagents add 1 2 to conjugated ketones and aldehydes 10 this preference for direct addition is attributed to the oxophilicity of the cerium reagent which activates the carbonyl for nucleophilic attack 11 reactions edit organocerium reagents are used almost exclusively for addition reactions in the same vein as organolithium and grignard reagents they are highly nucleophilic allowing additions to imines 12 in the absence of additional lewis acid catalysts making them useful for substrates in which typical conditions fail 2 nucleophilicity of organocerium reagents despite this high reactivity organocerium reagents are almost entirely non basic tolerating the presence of free alcohols and amines as well as enolizable α protons 2 7 non basic tendencies in organocerium reagents they undergo 1 2 addition in reactions with conjugated electrophiles at the same time organocerium reagents can be used to synthesize ketones from acyl compounds without over addition as seen with organocuprates 2 reactivity and selectivity of organocerium compounds organocerium reagents have been employed in a number of total syntheses shown below is a key coupling step in the total synthesis of roseophilin a potent antitumor antibiotic 3 total synthesis of roseophilin using an organocerium reagent see also edit luche reduction references edit berger tassilo lebon jakob maichle mössmer cäcilia anwander reiner 2021 cecl 3 n buli unraveling imamoto s organocerium reagent angewandte chemie international edition 60 28 15622 15631 bibcode 2021acie 6015622b doi 10 1002 anie 202103889 pmc 8362106 pmid 33905590 1 2 3 4 5 6 liu h j shia k s shang x zhu b y 1999 organocerium compounds in synthesis tetrahedron 55 13 3803 3830 doi 10 1016 s0040 4020 99 00114 3 1 2 3 bartoli g marcantoni e marcolini m sambri l 2010 applications of cecl 3 as an envitonmentally friendly promoter in organic chemistry chemical reviews 110 10 6104 6143 doi 10 1021 cr100084g pmid 20731375 evans william j rego daniel b ziller joseph w 2006 synthesis structure and 15 n nmr studies of paramagnetic lanthanide complexes obtained by reduction of dinitrogen inorganic chemistry 45 26 10790 10798 doi 10 1021 ic061485g pmid 17173438 anwander reiner dolg michael edelmann frank t 2017 the difficult search for organocerium scp iv scp compounds chemical society reviews 46 22 6697 6709 doi 10 1039 c7cs00147a pmid 28913523 smith michael b 2017 01 01 chapter 11 carbon carbon bond forming reactions cyanide alkyne anions grignard reagents and organolithium reagents in smith michael b ed organic synthesis fourth edition boston academic press pp 547 603 doi 10 1016 b978 0 12 800720 4 00011 8 isbn 978 0 12 800720 4 retrieved 2023 12 03 1 2 imamoto t suguira y takiyama n 1984 organocerium reagents nucleophilic addition to easily enolizable ketones tetrahedron letters 25 38 4233 4236 doi 10 1016 s0040 4039 01 81404 0 carey francis a sundberg richard j 2007 advanced organic chemistry part b reactions and synthesis 5th ed new york springer pp 664 665 isbn 978 0387683546 carey francis a sundberg richard j 2007 advanced organic chemistry part b reactions and synthesis 5th ed new york springer p 665 isbn 978 0387683546 imamoto tsuneo sugiura yasushi 1985 04 16 selective 1 2 addition of organocerium iii reagents to α β unsaturated carbonyl compounds journal of organometallic chemistry 285 1 c21 c23 doi 10 1016 0022 328x 85 87395 2 issn 0022 328x berger tassilo lebon jakob maichle mössmer cäcilia anwander reiner 2021 07 05 cecl 3 n buli unraveling imamoto s organocerium reagent angewandte chemie international edition 60 28 15622 15631 bibcode 2021acie 6015622b doi 10 1002 anie 202103889 issn 1433 7851 pmc 8362106 pmid 33905590 carey francis a sundberg richard j 2007 advanced organic chemistry part b reactions and synthesis 5th ed new york springer p 666 isbn 978 0387683546 v t e compounds of carbon with other elements in the periodic table ch che cli cbe cb cc cn co cf cne cna cmg cal csi cp cs ccl car ck cca csc cti cv ccr cmn cfe cco cni ccu czn cga cge cas cse cbr ckr crb csr cy czr cnb cmo ctc cru crh cpd cag ccd cin csn csb cte ci cxe ccs cba clu chf cta cw cre cos cir cpt cau chg ctl cpb cbi cpo cat rn fr cra lr rf db csg bh hs mt ds rg cn nh fl mc lv ts og cla cce cpr cnd cpm csm ceu cgd ctb cdy cho cer ctm cyb cac cth cpa cu cnp cpu cam ccm cbk ccf ces fm md no legend chemical bonds to carbon core organic chemistry many uses in chemistry academic research no widespread use bond unknown retrieved from https en wikipedia org w index php title organocerium_chemistry oldid 1370284201 categories organometallic chemistry organolanthanide compounds cerium hidden categories articles with short description short description is different from 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