7 Baran lab Group Meeting force Metal Pairs eae Tetered Heteropinetalic Systems. Represeriatve examples TrZrrogosolocive OH cchvaion nya rations Tan re Mo me 4 We PAu R doe he. a Fc cry us Fc” ‘Cr 258 Vs 799% selectvty ‘Suni avg Chom 2014, 53,6634 Pir tandem cos covsng-tantrhycrogenaton i < Me OS ee A ty Shen AQ ob he 7 THER OTE, ‘Bimetallic pairs of Transition Metals (and some Lanthanises) ‘00% pa . rs ACS 11, 180 pe coma pert or Co2r Kumada cosecouping alas an . homes as: independent oxtayet . ‘Meroe ot potorece: an ‘wansition metals, " 6 Grignard ees, ee ee TU = Ametal catalyst combined with thesis, _ + "Br Smol% [2r-Co} somiaeets "Misti cahachampetn fy AN Te acer Process the tagahip of metal paling a, a oat Pel ° « Zero, mee won, mH srg Cr, 188,71. 78 a eeninen ef oe Fst cqgarmetatc process in inutile. ={ChenzalEconorcs Handbook. 2019) pine (Fo) ponaontiel (16%), aaa ator (1) “Theres 1.-Ayeengyen, erotnalehy ae, sion 760 10° teonsued in 209, Sowy decreasing {ue tonaw methods for ace aor ano! 7 (Wersant, oxo proces) ws Son, me No “Doveope dung Wl and published sn ater mw ke “AP, We (1950) tess =o ov ey & Cat (ecto) a itl source Later om oh sett nec ‘ diets. “60 dehyrogonases “hac owuttr ter aera NEAR pear Ry home} selodactaseydeby passng «Waar Shomisonretornoterat| CO-+ H_O<=BO0, +2H" +26 eee “dra, R, ACTE, 2008, 43,9004 Dabok PAG, 2000, 50,1067 eve, rponomet Chom 2082, 49-044, 221 (en,p)scot ace Thomas, Eso, 2011, 2029Josep Cornelia Metal Pairs fe eae ‘Gastro Stephens reaction (only Ou) Pé-Cu decarboxyiatve aration of aryl halides and benzolc acids (Goossen) ct wn OF OO" Oe Cf BE oS et toss eet ee reg ae oom are™ CL, oe 20.mah PPP Cl ed ed "So. 2 oe ieaeci a t on neon Pa asia, Tet, 6 ’ Pit ce i. Sonogastira, Tt Lett ees coved Ao we "Sonogashira Cues”! yp? co inte tepcese ca 7 a Nn cman Oe ro, base “a7, 03, 258 | Ar~OTS toa orowates 10°C. arom arc! a-cu Pej catalyzed dbibie 6-H arylation idles ‘repro woe LL. : “synthesis (Yamamoto) PaaS ay aa pon ate toawrama of Zr000Me 201m FOP)» » A ay Sp AGOARC oan CURE, 2 id 51% Ket 60 equiv eso oa ‘equiv nN st, feeceeree Raa aaare ot 60, TusoMe Ne 7 ys td beat od kal yi aaa Gee homey Pag Pag cocoon aaton nds Laos) A CO;H 20 moh Pd(MeCN)Cl, = TWSNS \ peek etd : is Sean agony WaLT 20 produce ACS, 200, 125, 7786 i “DwFDNso, 20°C Ny 17076" 3u Synthesis of aileny! Doronates from esters (Szab6) + +>20:1 a Boonies fom pope aioe ab) ae en ‘ ou + Byping SSF PAP 5 wo SA on aah sae! THF, 50° cof 7 bu " cu=Bpin OA! if Tarte pin-x ree Ae pot cx simon pean Se aa een ii AcJosep Cornelia Metal Pairs casbruaaa herds T\__ Pé-Rh Pauson-Khan-iype Reaction (leona) Pa-Ag Dituoromethylation arenes (@. Shen) mor Peale eee =n 150% Pa,dbe)s Tomer set ea wa “smart donb zomohs SPrAGCL Peg one — Zt eo THSOF (2 eau) Sar vn Eat "2 equv BSA, CO (Fam) Nau Pre, °C eae ro ame fe Peta Sis oe sai more Phypavort nu "Smt Pandbon yen Cn rs 98% enn y ~_—\ For separate etsecen: ah, Swng fore ss 00122 6771 net 7 Acs, 2000122 0220 “Papp gation ACB 1008, 121, 7208 A : Pann Enantioselective Alyc Ayaton Savamura Ni "heat re ° ° >= wy Ao-rociicrs 1 met PCO Ie ome : asp n Nee ait 1 mabe finoca CO) We tle Sy wari ~ once ewe Kom THE -a0°C. 0) ates sia a icing rb ia i i i Lr: se Oe pusen, 20 mas PnyPALPE, babs 13-26mor Pdzdoes M°O* fe - CHCl posed Yu sey Pate ff-10? <> parc] oh moda oe CE wat eB i oy? oy oo. 5 " : Pos, 0 hee pape ey Psu, 2a a fates, FA on 0 20 ,€° ‘Au. Ph TRAP in Pd not enantioselectvity ACS, 1996, 118, 8909Baran lab Group Meeting Josep Cornelia Metal Pairs 6/46 aL Alifation of proparayic alcohols ros) ms NFS Bioeng ay Faas gan @ Ete tte ONE Sone “ensio“ oan tnae Nel inne” o80e pnygio“Hr0sPhs ae ee ae he +7 smell BOORTHE Sin ay van J ca, Sitmarscion" ° Mo sy, 1996638 i moe, 206 Nia ere eee Ns ACs, 2011 133, 12828 og TOU, ae Pao vin YisthnPatenercusycadenien: tee, sane aon ten Naso, + Alley ya | + les Tite MS Mier KR Nec Ha gg repaaton tien conve ora) Wie ACE 1,048 te " wet! B00, ” 8 OR, POY, taimcox OW, sf ane, N08 Men, — Aes Ny ase Be st 12 ecu crcl Ch aresta complex "CHO G1 mOMENICI, go, Oreos! J.Qhem. $06. Shem. Conia 876 98, fists SepscedstaeeLoancTs ia "A Aiton of pyines (aia) 84 2, ‘oreors 2 mee 4 a Gan oon ‘ Sree rae Simla yin CrCl (80 ea.) Ja. ses ramon. see (+ 7) _ somo emanate A non regure oval ACS ae, 1a, Ste eee ap "mat Nozaki Fyn, Ti, 1868, 24 8261 Fane ica sea aA cade 30535 Q Buty groups at 7 Alprovont C2 Ni-Cr-(Mn) catalte NHK (Furstner) on 1 one. 15 mot CrCl, Cr: CL (copped wih cat Nt ome Taser” te ‘OMe uF-DME, 50° bad peepee ier Con Rly by cataytic NIGlp R_CrlX L u l ai : NN A rye taco com 10 mote mICOO), % Bomorst gale 20 mots Alios , \— Pte, 80°C HL Ph pt Pe era an, Sie, 128 TeJosep Cornelia Metal Pairs See eae LN-TI(in) Enanfioselocive reductive arylation of meso epoxides (Wei) NiPa(2n) Gross-Ulimann reaction wih aryl halides and tates (We) 1 mels Ho, a FG 10 mote Nil ame Me mot Nibipv)Bee Moroney a Of Sole Palapprclns — zeae, na 2 eau >) reqvELNHC! — “Saw, sone Se we ud 2 Tcl, Natio, 2018, 254, 884 ‘Somcart| . ex ened ine ™ ‘cone Z sn fox om 1 equiv CaF Pie, 80 ok vo . oe on Orr e,,si-cut = ACS, 2014, 136, 2238 smo core i a Sato a dai aa i) Ph~~oMs 10 mol NiBr,- 3 H,0 ‘OMe om steed ‘oman ene ; an DMA cogr_l0mere diy foe CO peone Bea, er Nal, Zn, OMA, 60%> 4” 620% wx ] COL, Gannon ottoman mers Brera Om at 2,204 : “a Ee are oe CS a KtFtom.)- 94:0 reese —> CC : oxane,0 11 , ees ae —— 2s coat. GES ‘Ghee Set oes, a 21s | Ac toeJosep Cornella Metal Pairs Se reuie e ret Fe-Zn Reduce alkyl vinylation (X. Hu) Aon Tr-Mo Alkane metathesis (Goldman & Brooktart) a E10 mol Feb, Gi cat i} . ON thr RR, apes _ Ay, Lalit am é oO en om nO am SB nS wae BBR ate, weno, Ba, TOES 7 7 = td (Mo) OO er a ee Me. A anol a w 2Fot + Zn ACS 018,197, 4900" aw ca sas ae inde dockcaabapaisvoneenaaed et el ale dda ual lasses osc " pees i eon ia fae [ne curing rs - * pon SPHCHFOESIEO cory ite ane (aber = OO rm eee, CS ce ow fi es eee Ohh solvent : Awe call) Me Me weg an reek ue Sieh OTe yon Q : ~~ ee me ogy eee sa \Prcu-H ACS, 2013, 135, 10302 cy" equ ep = + SR omc acetic Me NR oman Soe |e me opel Un oo Te 28eq OOo eT ‘ ; ‘Natu, 2015, 517,351Josep Cornelia Metal Pairs Baran lab Group Meeting eae ‘Agila Asymmetie Conia Ere reaction (Shibasah) Mn-Cu radical cyclzations trom oxidation of acalc C-H bonds (Bary Snider) 2G — smoretaioiPes 10 moi L* A Mn(OAc),’ 2H, Seminar: Voica (2010) ny Faget Age pn Malone 2 AKG => sion ae SSB ee * oo meri fat AcOEt 07 Heioa, osiau,Koonl Am Chom, Soc 1968, 99,5905, uch Friant J. Am. Chem. Soc 1988, 90,5905 7 a ° OMe zac 3h ony Mo(OAe}y 24-0, COME some Fore 20-0 | eee rie ao “sie on ‘Snider: "Mondeo ontiry an bonayic oY NS {00,Me _butrot primary or secondary radical ee ee ame £O;:Me tod AL ‘Ag-Ru Trans-selective hydrogenation of alkynes (Mankad) euenonehay = atm momevigtrioming an 4 9 Raetleneome A euone ve 10-0 cy cue oh \ Me i Bish” oi 27 naroe nsyanest Imes—Ag—H "TBSO. 0s o og, wn o unre, l > rR L? east: oF} ak ca ae Me“ Me Me“ Me: = * sero wn <8 stn we “ne he iF ea we EEE oe nce a 7, ws | “teylitinane we Y? Danishoohy, JACS, 2000, 122, 6160Baran lab Group Meeting Josep Cornella Metal Pairs ‘eae a aaa a Te See sti on eanory 4 nn ne HL ie ae ia {Ra Ra! momumy, uACS, 1974, 96, 4708 Ro} fou ° 10 mots Th a | we ri af be an rMsc 8% zt, stag tata Fre to developed te T ponder tod, ting powder MSC mitre ae Gena yuan of neatrated ie (aobee) Coe el f zat a ee ed i ET 2 Tiel, jel in, snvanovouta | RSC i 4 nysicl™ 2 (To) Mn-Rh Hydroformation (Garland) JACS, 2015, 137, 8912 AusFe Synthesis of oxazole aldehydes (Jiao) JACS, 2008, 125, 6540 Pt-Zn Hydroformylation and hycroesterfcation of olefins (Hida) I. Mol. cata. 1986, 95, 29