Palldium-Catalyzed Coupling Chemistry 2017 by Acros

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Catalog Palldium-Catalyzed Coupling Chemistry 2017

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phosphine ligands have recently been replaced in a number of palladium cata­ly­sed reactions with n-heterocyclic carbenes nhcs 3 cl n oh b n cl oh pd 2 dba 3 c s 2 co 3 dioxane 13036 these ligands offer similar electronic properties to phosphines being strongly σ-donating and weakly π-acidic nhcs can offer very high catalytic activity combined with stability and longevity in comparison with phosphine ligands the carbene is air sensitive but can be generated in situ to aid operational simplicity r cln n base r r -hcl nnrn pdoac2 base n r n-heterocyclic carbene we offer a range of commonly used nhc precursors for use in cross coupling reactions n n cl cl 37831 35619 n n bffb f f 35620 38242 references 1 galardon,e ramdeehul s brown j.m cowley a hii k.k jutand a angew.chem int ed 2002 41 1760-1763 2 tolman c a chem rev 1977 77 313–348 3 for a review see hillier a.c grasa g a viciu m.s lee h m yang c nolan s p j organomet chem 2002 69-82 4 nfffnnn r r

suzuki chemistry is well known to be accelerated by the use of microwaves to heat the reaction.5 o o oh nh ho n b na2co3 toluene 150oc 15 mins n cl pddppbcl2 hn n n mw 35903 mo08305 it can also be used to perform aromatic alkylations.6 c-h insertion negates the necessity to begin with an aryl halide improving the atom efficiency of the process o oh other organoboron species such as trifluoro­ borate salts can also be used in this reaction.7 ho b oh o pdoac2 kh2po4 oh ag2co3 benzoquinone t buoh 100oc 34467 30926 2 the stille coupling r x r snr 3 pd0 the stille reaction is an extremely versatile alternative to the suzuki reaction it replaces the organoboron reagents with organostannanes as the tin bears four organic functional groups understanding the rates of transmetallation of each group is important relative rate of transmetallation alkynyl > vinyl > aryl > allyl ~ benzyl   alkyl the stille coupling is

it can be used to synthesise a wide range of compounds including styrenes,8 aromatic ketones9 and biaryl derivatives.10 the stille-kelly coupling the stille-kelly coupling is a palladium catalysed intramolecular cross coupling using distannanes such as hexabutyl­distannane or hexamethyldistannane i n pdcl2pph32 o i the intermediate mono-halide mono-stannane cyclises under the reaction conditions to yield the desired product.11 me3sn-snme3 xylene reflux n o 3 the negishi coupling r x r znx pd0 r r the negishi coupling utilises organo-zinc reagents as starting materials to cross couple with organohalides and equivalents the method is compatible with a good range of functional groups on the organohalide including ketones esters amines and nitriles the organo-zinc reagent can be prepared in situ by a variety of methodologies such as transmetallation of the corresponding organo-lithium or grignard reagent,12 or via oxidative addition of activated zn0 to an organohalide.13 n h 15195 i

4 the kumada coupling r x r mgx pd0 r the cross coupling of organohalides with grignard reagents is known as the kumada coupling although it suffers from a limited tolerance of different functional groups the higher reactivity and basicity of the grignard reagent allows viable reactions to take place under mild conditions.14 r o o mgcl pddba2 dppf meo meo o thf -40 c n 25258 n cl rf04027 5 the hiyama coupling r x r sir 3 pd0 base organosilanes can also be coupled with organohalides or their equivalents using palladium catalysts as with the suzuki reaction the transmetallation will not occur without activation by base or fluoride.15 the use of a silanol as the organosilane is one recent method that has managed to negate the requirement for the reaction to contain fluoride as an activator.16 this has helped to enlarge the substrate scope available to organic chemists r r meo meo meo ome si meo tbaf dioxane 80oc br 10663 pdoac2 dabco 37064 references 14 bonnet v mongin f

6 the sonogashira coupling r x r pd0 cui base r r the sonogashira reaction offers an extremely useful route into aryl and alkenyl-alkynes the alkyne moiety is usually introduced via its copper salt this is generated in situ from a cui salt such as cui or cucn and a terminal alkyne in the presence of an amine base.17 in this case the tms protecting group can be removed following the reaction to give the terminal alkyne product this can be further functionalised possibly via a second sonogashira coupling o o pdpph32cl2 cui et3n thf br si 20357 10667 recent improvements in this reaction have led to the development of copper and amine free couplings.18 si meo meo pdpph32cl2 tbaf br 15246 10663 other uses for this reaction involve the synthesis of intermediates that continue to react under the conditions to give more interesting products.19 n br n pdpph32cl2 cui n dbu dma n cc04010 n n references 17 thorand s krause n j org chem 1998 63 8551-8553 18 liang y xie y x li j h j org

7 the heck reaction r x r pd0 r r the heck reaction follows a slightly different pathway to other palladium catalysed couplings for intermolecular reactions with monosubstituted olefins the olefin insertion step is usually directed by steric hindrance this intermediate then undergoes β-hydride elimination under thermodynamically controlled conditions leading to preferential formation of the e product rxrl pd l pd l x r’ hx ch2 base h l pd l syn-olefin insertion -hybride elimination r’ l x r pd x r 10 l oxidative addition r’

9 palladium catalysed cyanation the palladium catalysed cyanation of aromatic halides offers a convenient alternative to the rosemund-von braun reaction which often employs harsh reaction conditions and can have a labour intensive workup as the cyanide nucleophile is a strong σ-donor and can poison the catalyst it is necessary to keep its concentration low during the reaction to achieve this zncn2 is often employed as the cyanide source as its solubility in dmf a common solvent for this reaction is limited.23 f pd2dba3 dppf n cl n f n zncn2 zn powder dma mw 100oc n n 42981 an alternative non-toxic source of cyanide has also been reported k4[fecn6 can be used in combination with palladium catalysts to synthesise aryl nitriles from their corresponding halides.24 br n pdoac2 dppf k4[fecn6 na2co3 dma 140oc s s 14780 this work was later extended to enable the reaction to take place without the need for the phosphine ligand.25 br o pdoac2 k4[fecn6 na2co3 dma 140oc ome o ome 41407

10 palladium catalysed carbonylation r x o pd0 r co nu base nu nu r o r r n h as with most palladium mediated c-c bond forming reactions palladium catalysed carbonylation is compatible with a range of functional groups this gives it significant advantages over standard organolithium and grignard chemistry for the synthesis of aryl aldehydes acids esters and amides pdphcn2cl2 0.1 mol dppf 0.6 mol co 25 bar n cl obu n et3n 1.2 eq n-buoh 130oc o 11001 esters and amides are synthesised by car­ bonylation in the presence of the required alcohol26 or amine nucleophile.27 n h 10706 the use of triethylsilane as the nucleophile gives the corresponding aldehyde as the product.28 o pdphcn2cl2 1 mol dppf 3 mol co 25 bar br n h et3n 1.5 eq toluene 130oc n n h 14718 br o n h [pdcl2dppp 2.5 mol co 3 bar hsiet3 2 eq na2co3 1 eq dmf 90oc o h o 17157 n h references 26 beller m mägerlein w indolese a f fischer c synthesis 2001 1098-1110 27 kumar k zapf a michalik d tillack a

monodentate ligands bidentate ligands general ligands general ligands cat no ligand name cas no cat no ligand name cas no 14042 29480 42232 32113 42161 38683 42842 42783 31733 13934 38338 triphenylphosphine tri 2-furylphosphine tri-o-tolylphosphine trimesitylphosphine 603-35-0 5518-52-5 6163-58-2 23897-15-6 tricyclohexylphosphine 2622-14-2 triisopropylphosphine tri-n-butylphosphine di-tert-butylmethylphosphine 6476-36-4 998-40-3 6002-40-0 36089 36694 tri-tert-butylphosphine 13716-12-6 29361 14791 36385 31005 38112 29646 32085 38337 34801 36387 42971 36375 2071-20-7 1663-45-2 23743-26-2 6737-42-4 103099-52-1 7688-25-7 27721-02-4 166330-10-5 12150-46-8 97239-80-0 84680-95-5 13991-08-7 buchwald type ligands cat no ligand name 38972 38714 35621 35622 35623 38009 38008 38007 38006 42983 42984 2 dicyclohexylphosphino 2’isopropylbiphenyl 2 dicyclohexylphosphino 2’,4’,6’triisopropylbiphenyl 2 di-tert-butylphosphinobiphenyl 2 dicyclohexylphosphinobiphenyl

palladium catalysts and precursors catalyst precursors cat no catalyst precursor name cas no 20683 20945 20790 29197 19518 19519 19520 36967 31702 allylpalladium chloride dimer bisacetonitrilepalladiumii chloride bisbenzonitrilepalladiumii chloride bisdibenzylideneacetonepalladium palladiumii acetate palladiumii bromide 12012-95-2 14592-56-4 14220-64-5 32005-36-0 3375-31-3 13444-94-5 palladiumii chloride 7647-10-1 palladiumii trifluoroacetate tetrakisacetonitrilepalladiumii tetrafluoroborate trisdibenzylideneacetonedipalladium0 trisdibenzylideneacetonedipalladiumchloroform adduct 42196-31-6 36352 31877 36934 21797-13-7 51364-51-3 52522-40-4 catalysts cat no catalyst name 38403 34868 36351 37797 20927 19732 29925 36350 21299 37796 39589 20238 36971 [1,2-bisdiphenylphosphinoethane dichloropalladiumii 1,1’-bisdiphenylphosphinoferrocenepalladiumiidichloride dichloromethane adduct bistricyclohexylphosphinepalladium0 bistriethylphosphinepalladiumii chloride

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