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transfer hydrogenation 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 organometallic catalysts 2 metal free routes 3 organocatalytic transfer hydrogenation 4 see also 5 references toggle the table of contents transfer hydrogenation 7 languages čeština deutsch euskara français italiano 日本語 中文 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 addition of non molecular hydrogen to a compound in chemistry transfer hydrogenation is a chemical reaction involving the addition of hydrogen to a compound from a source other than molecular h 2 it is applied in laboratory and industrial organic synthesis to saturate organic compounds and reduce ketones to alcohols and imines to amines it avoids the need for high pressure molecular h 2 used in conventional hydrogenation transfer hydrogenation usually occurs at mild temperature and pressure conditions using organic or organometallic catalysts many of which are chiral allowing efficient asymmetric synthesis it uses hydrogen donor compounds such as formic acid isopropanol or dihydroanthracene dehydrogenating them to co 2 acetone or anthracene respectively 1 often the donor molecules also function as solvents for the reaction a large scale application of transfer hydrogenation is coal liquefaction using donor solvents such as tetralin 2 3 organometallic catalysts edit in the area of organic synthesis a useful family of hydrogen transfer catalysts have been developed based on ruthenium and rhodium complexes often with diamine and phosphine ligands 4 a representative catalyst precursor is derived from cymene ruthenium dichloride dimer and the tosylated diphenylethylenediamine these catalysts are mainly employed for the reduction of ketones and imines to alcohols and amines respectively the hydrogen donor transfer agent is typically isopropanol which converts to acetone upon donation of hydrogen transfer hydrogenations can proceed with high enantioselectivities when the starting material is prochiral rr c o me 2 choh rr c h oh me 2 c o where rr c h oh is a chiral product a typical catalyst is cymene ru r r hnchphchphnts where ts refers to a tosyl group so 2 c 6 h 4 me and r r refers to the absolute configuration of the two chiral carbon centers this work was recognized with the 2001 nobel prize in chemistry to ryōji noyori 5 another family of hydrogen transfer agents are those based on aluminium alkoxides such as aluminium isopropoxide in the mpv reduction however their activities are relatively low by comparison with the transition metal based systems transfer hydrogenation catalyzed by transition metal complexes proceeds by an outer sphere mechanism the catalytic asymmetric hydrogenation of ketones was demonstrated with ruthenium based complexes of binap 6 7 even though the binap ru dihalide catalyst could reduce functionalized ketones the hydrogenation of simple ketones remained unsolved this challenge was solved with precatalysts of the type rucl 2 diphosphane diamine 8 these catalysts preferentially reduce ketones and aldehydes leaving olefins and many other substituents unaffected complementing traditional diphosphine based noyori catalysts are arene ru catalysts which operate similarly 9 the stoichiometric asymmetric reduction of ketones has long been known e g using chiral borones 10 metal free routes edit see also reductions with diimide and quinone prior to the development of catalytic hydrogenation many methods were developed for the hydrogenation of unsaturated substrates many of these methods are only of historical and pedagogical interest one prominent transfer hydrogenation agent is diimide or nh 2 also called diazene this becomes oxidized to the very stable n 2 transfer hydrogenation the diimide can be generated from hydrazine or certain other organic precursors two hydrocarbons that can serve as hydrogen donors are cyclohexene or cyclohexadiene in this case an alkane is formed along with a benzene the gain of aromatic stabilization energy when the benzene is formed is the driving force of the reaction pd can be used as a catalyst and a temperature of 100 c is employed more exotic transfer hydrogenations have been reported including this intramolecular one transfer hydrogenation many reactions exist with alcohol or amines as the proton donors and alkali metals as electron donors of continuing value is the sodium metal mediated birch reduction of arenes another name for aromatic hydrocarbons less important presently is the bouveault blanc reduction of esters the combination of magnesium and methanol is used in alkene reductions e g the synthesis of asenapine 11 magnesium methanol reduction in asenapine synthesis organocatalytic transfer hydrogenation edit organocatalytic transfer hydrogenation has been described by the group of list in 2004 in a system with a hantzsch ester as hydride donor and an amine catalyst 12 in this particular reaction the substrate is an α β unsaturated carbonyl compound the proton donor is oxidized to the pyridine form and resembles the biochemically relevant coenzyme nadh in the catalytic cycle for this reaction the amine and the aldehyde first form an iminium ion then proton transfer is followed by hydrolysis of the iminium bond regenerating the catalyst by adopting a chiral imidazolidinone macmillan organocatalyst an enantioselectivity of 81 ee was obtained 13 in a case of stereoconvergence both the e isomer and the z isomer in this reaction yield the s enantiomer extending the scope of this reaction towards ketones or rather enones requires fine tuning of the catalyst add a benzyl group and replace the t butyl group by a furan and of the hantzsch ester add more bulky t butyl groups 14 with another organocatalyst altogether hydrogenation can also be accomplished for imines one cascade reaction is catalyzed by a chiral phosphoric acid 15 the reaction proceeds via a chiral iminium ion traditional metal based catalysts hydrogenation of aromatic or heteroaromatic substrates tend to fail see also edit meerwein ponndorf verley reduction oppenauer oxidation dehydrogenation hydrogenation hydrogenolysis borrowing hydrogen references edit wang dong astruc didier 2015 the golden age of transfer hydrogenation chem rev 115 13 6621 6686 doi 10 1021 acs chemrev 5b00203 issn 0009 2665 pmid 26061159 speight j g the chemistry and technology of coal marcel dekker new york 1983 p 226 ff isbn 0 8247 1915 8 muñiz kilian 2005 bifunctional metal ligand catalysis hydrogenations and new reactions within the metal di amine scaffold13 angewandte chemie international edition 44 41 6622 6627 doi 10 1002 anie 200501787 pmid 16187395 t ikariya k murata r noyori bifunctional transition metal based molecular catalysts for asymmetric syntheses org biomol chem 2006 volume 4 393 406 shimizu hideo nagasaki izuru matsumura kazuhiko sayo noboru saito takao 2007 developments in asymmetric hydrogenation from an industrial perspective accounts of chemical research 40 12 1385 1393 doi 10 1021 ar700101x pmid 17685581 mashima k kusano k h sato n matsumura y i nozaki k kumobayashi h sayo n hori y ishizaki t 1994 cationic binap ru ii halide complexes highly efficient catalysts for stereoselective asymmetric hydrogenation of α and β functionalized ketones the journal of organic chemistry 59 11 3064 3076 doi 10 1021 jo00090a026 kitamura m ohkuma t inoue s sayo n kumobayashi h akutagawa s ohta t takaya h noyori r 1988 homogeneous asymmetric hydrogenation of functionalized ketones journal of the american chemical society 110 2 629 631 bibcode 1988jachs 110 629k doi 10 1021 ja00210a070 noyori r ohkuma t 2001 asymmetric catalysis by architectural and functional molecular engineering practical chemo and stereoselective hydrogenation of ketones angewandte chemie international edition 40 1 40 73 doi 10 1002 1521 3773 20010105 40 1 40 aid anie40 3 0 co 2 5 pmid 11169691 dub pavel a gordon john c 2018 the role of the metal bound n h functionality in noyori type molecular catalysts nature reviews chemistry 2 12 396 408 doi 10 1038 s41570 018 0049 z s2cid 106394152 m m midland 1989 asymmetric reductions with organoborane reagents chemical reviews 89 7 1553 1561 doi 10 1021 cr00097a010 linden m v d roeters t harting r stokkingreef e gelpke a s kemperman g 2008 debottlenecking the synthesis route of asenapine organic process research development 12 2 196 201 doi 10 1021 op700240c yang hechavarria fonseca m list b 2004 a metal free transfer hydrogenation organocatalytic conjugate reduction of alpha beta unsaturated aldehydes angewandte chemie international edition in english 43 48 6660 6662 doi 10 1002 anie 200461816 pmid 15540245 ouellet tuttle j macmillan d 2005 enantioselective organocatalytic hydride reduction journal of the american chemical society 127 1 32 33 bibcode 2005jachs 127 32o doi 10 1021 ja043834g pmid 15631434 tuttle ouellet s macmillan d 2006 organocatalytic transfer hydrogenation of cyclic enones pdf journal of the american chemical society 128 39 12662 12663 bibcode 2006jachs 12812662t doi 10 1021 ja0653066 pmid 17002356 s2cid 12456921 rueping antonchick a theissmann t 2006 a highly enantioselective brønsted acid catalyzed cascade reaction organocatalytic transfer hydrogenation of quinolines and their application in the synthesis of alkaloids angewandte chemie international edition in english 45 22 3683 3686 doi 10 1002 anie 200600191 pmid 16639754 retrieved from https en wikipedia org w index php title transfer_hydrogenation oldid 1311937529 categories chemical processes organic redox reactions hydrogenation hidden categories articles with short description short description is different from wikidata this page was last edited on 17 september 2025 at 19 04 utc page was rendered with parsoid text is available under the creative commons attribution sharealike 4 0 license additional terms may apply by using this site you agree to the terms of use and privacy policy wikipedia is a registered trademark of the wikimedia foundation inc a non profit organization privacy policy about wikipedia disclaimers contact wikipedia legal safety contacts code of conduct developers statistics cookie statement mobile view search search toggle the table of contents transfer hydrogenation 7 languages add topic