CAVINATO G

TONIOLO L

VAVASORI A.

Name not available

R.ldnH trom
JOURNAL OF
MOLECULAR
CATALYSIS
Synthesis of 7-ketocarboxylic acids via reduction of
fketo-d-hydroxycarboxylic acids wifh carbon
monoxide catalyzed by a Pd-HCI system
G. Cavinato', L. Tolioloa*. A- Vavasn'
'ùNtued i, tu@k cr6ba. urtuBtd
ELSEVIER
cafatYsts
Synthesis of y-ketocarboxylic acids via redùction of
yketo-a-hydroxycaîboxylic acids with carbon
monoxide catalyzed by a Pd-HCl system
C. Cavinalo', L TonioloL*, A vavasorib
a f m H . d @ i  ; ! o ! n  -  + .
îvdo, ;d;r oddqs ù: Pd ,Go
,6  ro , "d r . " . rm c '  oqc: : r q . . " . " - -
- -u  a , - * i * ^  * ,a "p4  ' oodd t rn  i ds  to .  . ! . h ' s r ' , d {  r '
^ " i u  r ^  * " . * t r ,  $ i l *h ig r
Ko lH . t sc | .ooH 'úJ ' * i " i .
a * - . . * . a e u l , .
; , m  - " . d ; F . . J , s d  ' H c
r- ;.'- È -';'; h; ." . &
;,".ú".qrcctsfrrcù \"'
i . p , ì . r " a r c . - +  b P d !  { q . P d  Í
dfld.E!Pduiùf ldúLd

ldim(rÌ) p@ù6ù ùd Òf Hcì and H,o, 'he t0f
or HO dr pl.dùd fom ir poùr yi.ld
Phcmr!cHoHcooH+ co - PhcocH,cHzcooH+ co:
l0m/3Gr000/ l0o 1000 (moD I tnpd!toF: lci]-l ldcr tPdl: l0 i b lù I Mì sL
.aÌsiydc prccuEùs tisrd in Tsbto I deompos
to prlldiM ebl. TlÉ .xe ol the d(ompsiriq drFnds on rh. Èdion condiriois.
adiÈ'jv. ob$nrions show 'hd Pdc!(PPhr)? k hs sbblè r hichfttnÉnìùq hish.r
.onadfuúorgqandofH,o'ad
p,tbdim I r2l. strgsBr 'ra! u& Educ
PPIìr hy Hq rono*.d by riucdù b Pd(o) by co. vhi.h is diidi?d b co, in rhe
Pdcr:(Pn r)?r-ì I pdo,t: +pdct ,(co)"-
Pdcl-"(co)"- lcooH)+ Pd(o) +cq
ds v rh co r sùpft riosPhùL! I's$tu ( j0 30
dm). i r20'c. ro sNe,hc rút, Pd:cLr(co):. vhch qulrrv itoiipors ro ! der
I  f . r i . o ,  ' d  r  ' l  f p
!iL thr di'is lPd:cLr(PPhnl md rtu momnÙ Pdcrr(PPh,), tlrl. 'hus nrudiùnrÉvesir! relcrùn (l) The redrtiùn P
fc{hohydmxypn lrdi!Frrr), rIft h I
!ùhonyl iga.d 1s htirlÉp'oposd.rhlrrccldc)
ir) ri1d. nrdinls {ss6r,rú dÈ !
*,,.,;rù"0"-"*.-pby"d.i.p.
by  Pd  HcL ! rù  L r0  1 l l
A5aLimdrmen,in{d.rcdion ( L)rt
dùe tundior or Ho n ro tnm lhrÒnde (A) rhr
tcH(cooH)cH,coPhl óùi.rv (se s.hcmc L) oridr't
hi 4 I rrxll. Redu(odPdlldiùmi\
hrcùru d rvpc rp) n4 odnhí hqt ùe
ryzcdcÍboùùliontdio6l L? l 2sl andùÙ.
ùe (r3) frfìa,hr Nd.opl icnú.k
I
I
}|do.hlodd.cHrcocg]cgrc]IoÈvu
Iftc(n:fgE{\+hcH,cH?@HrÈc|2M,+Pfo)rco'+4c|
(4 i @r \, (") ,r?o
|  
" 0 \ 6't lco.H, Iìi]g,c.H@.k d +sl]@rcr(@H)2 +o')t , {)l rc,
' qooe I
PùcootÍs-pd-cr P@cHdtGPLcl
,tD | @, ",'"1',o
PúH4r-ft-c' emcH2G'óoH ì fd(o) ' Ho
"Ì", |-' 
(P)
I
$ k r y | f u @ d . d F . F ù q s I Ù ú o i f u B ú h c a H Í n l M H ù } E d l c , o À d
a (p) h3ve d$ be.n pmposd in ordd ro e.óùitfÒr.h! tush cf,lyricariviry obs.d.4
.onpeble'o'hdorú.syrotuhercrcpon.d t301.
Irì r.p ( ii), iobdim ofH:o 4d co on ft. nrd yielÀ inr.m.lirc ( b) h,viq aìs
I cùbohyndy \gad. T1ìù ùh.di,r, ahr piydid. abs@ùoi ffon rhe cùb.hy,
dDxy lcad ciE otr co: ( r.p iit [rl I md yierds rcdEriv..ìimìmrion ofpodld (p)
chioriè rrd ì. Iikely ro rom on ùc sufic. of rre neìzi) my lar *irh rhè qúrrric
inrefnediaG (r). ynrding diEdty rh. fii'l pódúr ( !Èp r, *irhoú my d..:Ìhoxybrjdples, md i Pd(tr) spejd wùich is Edued by co ro Pd(0) j Érdy rù ùorhèf qùìr4ic
.ycre h o'df ro suppon rhis posibìl
ofPd/c.dll0qc'utrddDih€eifmos
rhè. ondnio$, rh. kersr ond. úd ro
( r ). in .onra! rù pdhdimì hdr
rfumelil{ ( d) mdùgÒs dsiibq
,  t r , , o , t -  . e t  . i  o 3 r r , - ,  , e .  o , p . r ! , o
s'$ i. Li rtrd-viii ùc úmmorry rr$d itr FLridirù o;Lyzed ato0ryhhn d
d ,  n ' t d .o '  '  o '  t , {  s
. '  * , : ' " 1  ' '  t r t r  r |  ' '  r I t r '  ' ' ' 4  \
Dicanriiìoùd (a 5%) of phcocH:cH.cooH
' :+ù :mo]  q ' '  n  \
Pdclr(PPhr):, IPdcL(PPhr)1,. Ipdo(1 r rciHJlr.pd(pFhrr lcepqrrcdiolo*
r ). PQùdidldtjtoti lnaÌt anrlsi
" ; "  ' ' " '  r 'q '  '
3.r stù{h aJPhcocHtcfllcooB qq lttúnotPrcacq:cHaqcoop vùh co
] n i l y p i . a ] e r p e n f . í . 0 0 , , n m o l o f q h l y s l
tuc@4cHoHcooH. 3 ml ordior
tmp . f l ù t ' l yP i c r ] ] y l | 0 . c . {Nc l
erp€.imeù ( 2 hl. 1ì. !ú{Ehve Qs .h
Usiislorofrheprìhdiunor) p€ùM6 rpon.d in rùb r orpd(pphl)rabrek o,rcr
J 4 A"?nlpktt co.ùnrklbÌ aJ P hcoc4zc4o4coo4 to phcoc Hzc Ht cooH ).
Fono{inc ú{ FEedùe jur dscnbed
PhcocH,crlcooH (59È), rbe rcmai
PhcocH.cH.coog !run
rcooH (HPLCllatysis).
oùn. or Rs.arch (c N.R ) for,onson0s ùh
Esùch ( tusdro FirahTaîo chimi.a Fine n) and dr Ersdú,! compùy of Mrù rd
i  r lr M ib*ùudr qirdhh4dh.,! rúúrúr.



Synthesis of g-ketocarboxylic acids via reduction of g-keto-a-hydroxycarboxylic acids with carbon monoxide catalyzed by a Pd-HCl system

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