TP CH PHT TRIN KH&CN, TP 11, S 08 - 2008

NGHIN CU S DNG BENTONITE BNH THUN BIN TNH LM XC

TC CHO PHN NG GHP I HECK GIA IODOTOLUENE V
STYRENE
Phan Thanh Sn Nam, Vng Quang Tho
Trng i hc Bch khoa, HQG -HCM
(Bi nhn ngy 10 thng 01 nm 2008, hon chnh sa cha ngy 12 thng 05 nm 2008)

TM TT: Xc tc bentonite Bnh Thun bin tnh c iu ch bng phng php

trao i cation vi dung dch PdCl2 trong dung mi nc. Hm lng Pd c trong xc tc l
0,14 mmol Pd /g (xc nh bng phng php quang ph hp thu nguyn t), v b mt ring
BET ca xc tc l 160,36 m2/g. Xc tc Pd iu ch c c hot tnh tt trong phn ng
ghp i Heck gia 4-iodotoluene v styrene. Phn ng c thc hin trong dung mi
dimethylformamide (DMF) nhit 120oC, vi s c mt ca Na2CO3 hm lng xc tc
nh hn 1 mol % Pd. Phn ng hnh thnh hai sn phm ghp i l trans-4-methylstilben v
1-phenyl-1-tolylethylene, vi t l tng ng khong 7,5:1 (c xc nh bng phng php
sc k kh v sc k kh ghp khi ph). Xc tc c tch ra khi hn hp phn ng d dng,
c kh nng thu hi v ti s dng. Kt qu nghin cu cn cho thy tc phn ng tng
mt cch ng k trong iu kin c s h tr ca vi sng.
1. GII THIU
Phn ng ghp i xy dng b khung carbon t nhng phn t n gin nh vo cc xc
tc kim loi chuyn tip v ang thu ht s quan tm ca cng ng cc nh khoa hc trong
sut hn 30 nm qua [1]. Trong , phn ng ghp i Heck gia cc dn xut halogen ca
hydrocarbon thm vi cc alkene u mch nh styrene v dn xut ca n c xem l mt
trong nhng phn ng quan trng nht, c ng dng rng ri trong ngnh sn xut cc ho
cht cao cp, sn xut cc dc phm quan trng cng nh cc vt liu k thut c tnh nng
cao [2,3]. Phn ng Heck thng s dng xc tc Pd dng ng th hoc d th, trong xc
tc Pd d th ang c quan tm do vn tch v tinh ch sn phm d dng hn, cng nh
xc tc d th s c kh nng thu hi v ti s dng tt hn ph hp vi hng i ca ha hc
xanh [4]. Ngy nay, ngi ta vn phi s dng cc xc tc phc Pd t tin cho phn ng Heck,
v cc nh khoa hc vn ang nghin cu vi mc ch s tm ra mt loi xc tc tt nht cho
phn ng ny [5].
Vic s dng bentonite Bnh Thun bin tnh lm xc tc cho cc phn ng tng hp hu
c c cc nh khoa hc trong nc nghin cu t nhiu nm qua, c bit l nhm
nghin cu ca tc gi Ng Th Thun v cc cng s i hc Quc gia H Ni [6,7]. Cc
nghin cu ni trn tp trung vo vic trao i bentonite Bnh Thun vi cc kim loi nh
Fe3+, Al3+, Zn2+ lm xc tc acid rn trong cc phn ng alkyl ho hoc ng phn ho, hoc
s dng bentonite Bnh Thun lm cht mang cho cc tc nhn oxy ho. Theo hiu bit ca
chng ti, mc d phn ng ghp i ni chung v phn ng Heck ni ring ang c cc
nh khoa hc trn th gii quan tm nghin cu nhng cc nhm nghin cu Vit Nam vn
cha c cc cng b v vn ny. Trong bi bo ny, nhm nghin cu ca chng ti cng
b cc kt qu nghin cu v kh nng s dng bentonite Bnh thun trao i vi Pd2+ lm xc
tc cho phn ng ghp i Heck gia 4-iodotoluene v styrene.

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Science & Technology Development, Vol 11, No.08 - 2008

2. THC NGHIM
2.1. iu ch xc tc
Bentonite Bnh Thun c s ch v tinh ch theo quy trnh cng b trc y ca
nhm nghin cu chng ti [8]. Bentonite tinh ch c hot ho bng dung dch HCl 10%
vi t l rn:lng l 1:22 (tnh trn khi lng kh tuyt i), khuy lin tc 70oC trong 6
gi. Hn hp sau em lc, ra bng nc ct cho n ht ion Cl - (kim tra bng dung dch
AgNO3), sy kh v nghin mn, thu c bentonite-H+.
Bentonite-H+ c tin hnh trao i vi dung dch mui PdCl2 0,016 M (PdCl2 c
cung cp bi Cng ty Kanto Chemical Nht Bn) vi t l rn lng l 1:8 (tnh trn khi
lng kh tuyt i), khuy lin tc 70oC trong 24 gi. Hn hp sau khi trao i xong c
em lc, ra bng nc ct cho n ht ion Cl- (kim tra bng dung dch AgNO3), sy kh v
nghin mn, ry qua ry 100 mesh, thu c xc tc bentonite-Pd2+, bo qun trong bnh ht
m.
2.2. Xc nh mt s c trng ca xc tc
Mu bentonite-H+ c xc nh ph nhiu x Rnghen ti Vin Du Kh Vit Nam, s
dng my Rnghen Siemens ca c trong iu kin ng pht tia bng Cu, bc sng K =
1,5046 , cng ng pht 35 mA, in p 40 KV, gc qut 2 thay i t 3-65o, phm lc
Ni.
B mt ring ca xc tc bentonite-Pd2+ c xc nh bng phng php hp ph BET
theo N2 77 K. Mu c o ti Phng Th nghim Phn tch thuc Vin Cng ngh Ho hc
TP. H Ch Minh.
Hm lng Pd trong xc tc bentonite-Pd2+ c xc nh bng phng php quang ph
hp thu nguyn t (AAS). Mu c o ti Trung tm Dch v Phn tch Th nghim TP. H
Ch Minh.
2.3. Kim tra hot tnh xc tc trong phn ng Heck
Hot tnh ca xc tc bentonite-Pd2+ c xc nh trong phn ng ghp i Heck gia 4iodotoluene v styrene. Quy trnh phn ng c thc hin da theo cc ti liu cng b
trc y [9]. Pha 250 ml dung dch gc ca 4-CH3-C6H4I trong cc dung mi tng ng, c
cha mt lng hexadecane C16H34 dng lm ni chun cho phn ng, vi t l mol 4-CH3C6H4I : C16H34 l 1:1.
Mi phn ng thc hin vi 5 ml dung dch hn hp ni trn, tng ng vi 0,12 ml 4CH3-C6H4I. Dung dch phn ng c cho vo bnh cu 2 c c cha sn mt lng xc tc
tng ng, v cho thm mt lng base tng ng vi t l mol 4-CH3-C6H4I: base c c
nh l 1:3. Sau cho 0,2 ml styrene vo dung dch phn ng, tng ng vi t l mol 4CH3-C6H4I : styrene c nh l 1:1,5.
Hn hp phn ng c nng n nhit thch hp bng bp khuy t gia nhit. Ti thi
im ban u v cch mi gi phn ng, dng kim tim ly 0,2 ml mu, ho tan vo 1 ml ether
v trch ly vi 1 ml nc ct. Tc cht v sn phm tan trong pha ether v base tan trong pha
nc. Pha ether c em i phn tch sc k kh (GC), t tnh chuyn ho ca phn
ng theo phng php da trn ni chun.
Sn phm ca phn ng cn c kim chng bng phng php sc k kh ghp khi ph
(GC-MS) vi iu kin: ct Agilent 19091s, 30 m x 0,25 mm x 0,25 mm x 0,25 m; detector

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TP CH PHT TRIN KH&CN, TP 11, S 08 - 2008

MS, kh mang helium, nhit injector 300oC, nhit detector 300 oC, vn tc kh mang 36
cm/s, chng trnh nhit nh sau:
60oC (1 pht)

5oC/pht

10oC/pht 145oC

100oC

25oC/pht 300oC (3 pht)

3. KT QU V THO LUN
Tng t nh cng b trc y ca nhm nghin cu chng ti khi iu ch xc tc
bentonite Bnh Thun bin tnh cho phn ng alkyl ho [8], kt qu ph nhiu x Rnghen ca
mu bentonite-H+ cho thy bentonite Bnh Thun hot ho bng dung dch HCl 10% cha
thnh phn ch yu l montmorillonite v qu trnh hot ha loi b hon ton lng
khong calcium. Kt qu phn tnh b mt ring BET cho thy din tch b mt ring ca xc
tc bentonite-Pd2+ l 160,36 m2/g. Kt qu phn tch quang ph hp thu nguyn t (AAS) cho
thy hm lng Pd c trong xc tc bentonite-Pd2+ l 0,14 mmol/g xc tc.
Hot tnh ca xc tc bentonite-Pd2+ c nh gi thng qua phn ng ghp i Heck
gia 4-iodotoluene v styrene (Hnh 1). Phn ng c thc hin trong dung mi vi s c
mt ca mt base. Sn phm ca phn ng l trans-4-methylstilben (I) v 1-phenyl-1tolylethylene (ng phn gem-) (II), trong sn phm chnh lun lun l trans-4methylstilben [4], l sn phm bn nht v c nhit si cao nht. Kt qu nghin cu trc
y ca chng ti cho thy sn phm ca phn ng Heck s dng xc tc bentonite bin tnh l
ng phn trans-, gem- v vt ca ng phn cis-, c phn bit da trn thi gian lu ca
cc cht chun (Sigma-Aldrich) trn sc k [10]. Kt qu ny tng t nh kt qu nghin
cu ca nhm nghin cu Varma v cng s Trng i hc Sam Houston State (Hoa K)
trong xc tc Pd c iu ch da trn khong st montmorillonite K10 [11]. Kt qu
phn tch sc k kh cho thy t l sn phm (I) : (II) vo khong 7,5:1. Ln lt kho st nh
hng ca cc yu t dung mi phn ng, loi base, nhit phn ng, hm lng xc tc ln
chuyn ho tng cng ca phn ng.
I
+

Pd
+

to
CH3
CH3
(I)

CH3
(II)

Hnh 1. Phn ng Heck gia iodotoluene v styrene

3.1. nh hng ca dung mi phn ng

Phn ng Heck s dng xc tc bentonite Bnh Thun bin tnh c thc hin trong ba
loi dung mi khc nhau: dung mi phn cc khng c proton l dimethylformamide (DMF),
dung mi phn cc c proton l ru isoamyl (C5H11OH), v dung mi khng phn cc l
xylene. Nhit ca phn ng l 120oC, base s dng l triethylamine (Et3N), hm lng xc
tc s dng l 0,5 mol% (t l mol gia Pd v 4-iodotoluene). Kt qu nghin cu cho thy
phn ng t chuyn ha tng cng cao nht khong 61,3% trong dung mi DMF sau 6 gi
phn ng, trong khi cc dung mi C5H11OH v xylene ch cho chuyn ha hu nh
khng ng k, di 2% trong cng thi gian phn ng (Hnh 2).

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Science & Technology Development, Vol 11, No.08 - 2008

80
chuyn ho (%)

DMF
isoamyl

60

xylene
40
20
0
0

2
3
4
Thi gian (h)

Hnh 2. nh hng ca dung mi ln chuyn ho ca phn ng (nhit 120oC, 0,5 mol% xc tc

Pd, base l triethylamine)

T cho thy DMF l dung mi thch hp cho phn ng Heck s dng xc tc bentonite
Bnh Thun bin tnh. C nhiu quan im cho rng cc dung mi phn cc khng c proton
nh DMF c kh nng gp phn h tr cho qu trnh kh Pd (II) v Pd (0), v Pd (0) mi l
xc tc thc s cho phn ng Heck [4,5]. Qu trnh kh Pd (II) v Pd (0) cng thun li th
cng thc y cho phn ng Heck xy ra. Cc dung mi khng phn cc nh xylene hoc phn
cc c proton nh ru isoamyl do khng giu in t nn khng h tr cho qu trnh kh Pd
(II) v Pd (0). Tuy nhin, c ch ca qu trnh ny vn cha c gii thch r rng trong cc
cng trnh khoa hc cng b.
3.2. nh hng ca loi base c s dng

Hnh 3. nh hng ca base ln chuyn ho ca phn ng (nhit 120oC, dung mi DMF, 0,5
mol% xc tc Pd)

Phn ng Heck gia 4-iodotoluene v styrene sinh ra sn phm ph l HI, v acid ny s

phn ng vi xc tc Pd. V vy, cn phi s dng mt base trung ha lng acid ny, ti
sinh li xc tc dng Pd (0) [2]. kho st nh hng ca cc base s dng, phn ng c
thc hin trong dung mi DMF nhit 120oC vi hm lng xc tc l 0,5 mol%. Cc
nghin cu trc y cho thy c th s dng nhiu loi base khc nhau cho phn ng Heck,
c th l base hu c hay base v c, ty thuc vo loi xc tc cng nh iu kin phn ng
[5]. Cc base c s dng cho phn ng gia 4-iodotoluene v styrene trong nghin cu ny
ln lt l triethyl amine (Et3N), Na2CO3, v CH3COONa.

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TP CH PHT TRIN KH&CN, TP 11, S 08 - 2008

Kt qu nghin cu (Hnh 3) cho thy trong giai on u, phn ng s dng base dng
ha tan l Et3N cng nh CH3COONa cho chuyn ha cao hn so vi trng hp s dng
base kh tan l Na2CO3. Do xc tc Pd s dng dng rn, lng HI sinh ra vn cn kt hp
vi cc trung tm Pd dng rn ny. V vy, qu trnh trung ha HI ph thuc vo qu trnh
khuch tn base vo bentonite. Trong giai on u, base Na2CO3 dng bt rn c tan
trong DMF thp hn so vi Et3N v CH3COONa nn phn ng tng ng cho chuyn ha
thp hn. Sau khong 4 gi phn ng, lng Na2CO3 tan trong DMF ln, chuyn ha
ca phn ng tng ln v t 61,3% sau 6 gi, cao hn so vi phn ng s dng Et3N (47,9%)
v CH3COONa (44%). Nh vy trong cc base s dng, Na2CO3 thch hp cho phn ng Heck
s dng xc tc bentonite bin tnh.
3.3. nh hng ca nhit
Trong nhiu nghin cu, phn ng Heck vi xc tc Pd rn c thc hin trong mt
khong nhit kh rng, khong t 80oC n 150oC, ty thuc vo loi xc tc v tc nhn
phn ng [4]. Nhit cao gip cho phn ng xy ra d dng hn. Tuy nhin DMF d b phn
hu mt phn nhit gn nhit si (153oC) nn trong nghin cu ny, cc phn ng
c kho st cc nhit ln lt l 120oC, 110oC v 100oC. Cc phn ng s dng hm
lng xc tc l 0,5 mol% v base l Na2CO3 trong dung mi DMF. Kt qu nghin cu
(Hnh 4) cho thy sau 6 gi phn ng, phn ng thc hin nhit 120oC, 110oC v 100oC
c chuyn ha ln lt l 61,3%, 37,7% v 6,8%.

chuynho(%
)

80
100

60

110
120

40
20
0
0

Thi gian (h)

Hnh 4. nh hng ca nhit ln chuyn ho ca phn ng (dung mi DMF, base l Na2CO3, 0,5
mol% xc tc Pd)

3.4. nh hng ca hm lng xc tc

Phn ng Heck gia 4-iodotoluene v styrene c kho st vi cc hm lng xc tc
khc nhau: 0,7 mol%, 0,5 mol% v 0,3 mol%. Cc phn ng c thc hin trong dung mi
DMF, nhit 120oC vi base l Na2CO3. Kt qu th nghim (hnh 5) cho thy sau 6 gi
phn ng, chuyn ha t c ln lt l 76% ( hm lng xc tc 0,7 mol%), 61,3% (
hm lng xc tc 0,5 mol%) v 20,7% ( hm lng xc tc 0,3 mol%). Kt qu ny tng
t nh nhiu nghin cu khc, trong tc phn ng tng theo hm lng xc tc s dng.
Tuy nhin do Pd l mt kim loi qu v xc tc c chi ph cao, trong thc t ty iu kin c
th m chn lng xc tc thch hp. Kt qu nghin cu cn cho thy xc tc bentonite Bnh
Thun bin tnh c hiu qu trong phn ng Heck hm lng Pd tng i thp.

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Science & Technology Development, Vol 11, No.08 - 2008

0.5%
0.3%
0.70%

chuynho(%
)

80
60
40
20
0
0

Thi gian (h)

Hnh 5. nh hng ca hm lng xc tc ln chuyn ho ca phn ng (dung mi DMF, nhit

120oC, base l Na2CO3)

3.5. Kh nng thu hi v ti s dng xc tc

Mt vn cn quan tm ca cc phn ng s dng xc tc rn l kh nng thu hi v ti
s dng xc tc. Sau khi cc phn ng kt thc, lng xc tc bentonite-Pd2+c lc ra
nhiu ln vi cc dung mi nh toluene, DMF, nc, ethanol loi b cc tc cht hp ph
vt l trn b mt xc tc. Sau xc tc thu hi c sy kh v s dng li cho phn ng
mi gia 4-iodotoluene v styrene. iu kin phn ng tng t nh phn ng vi xc tc
mi: dung mi s dng l DMF, base s dng l Na2CO3, nhit phn ng l 120oC, khi
lng xc tc thu hi v lng tc cht phn ng tng t nh trng hp phn ng s dng
xc tc mi. Kt qu nghin cu cho thy sau 6 h, phn ng s dng xc tc thu hi cho
chuyn ha 41,1% (phn ng s dng xc tc mi trong cng iu kin cho chuyn ha
61,3%). Nh vy mc d hot tnh gim, xc tc bentonite Bnh Thun bin tnh vn c kh
nng thu hi v ti s dng. Tuy nhin, vn ny cn c tip tc cc nghin cu tip
theo.
3.6. Thc hin phn ng trong iu kin c s h tr ca vi sng
Vic thc hin cc phn ng tng hp hu c trong iu kin c s h tr ca vi sng
(microwave) v ang thu ht s quan tm ca cc nh ha hc. Cc phn ng hu c thc
hin trong l vi sng c thi gian phn ng ngn hn nhiu so vi cc phng php gia nhit
thng thng [12]. Ngoi ra, cc nghin cu trc y cho thy vi s c mt ca vi sng,
chuyn ha ca phn ng c tng mt cch ng k [13]. Trong nghin cu ny, phn ng
Heck gia 4-iodotoluene v styrene c thc hin trong l vi sng gia dng Whirlpool,
Model AVM541/WP/WH c th iu chnh c cng sut v thi gian. Phn ng c thc
hin cng sut 800 W trong bnh cu c gn sinh hn hon lu nc t trong lng l vi
sng. iu kin phn ng tng t nh trng hp gia nhit thng thng: dung mi s dng
l DMF, base s dng l Na2CO3, hm lng xc tc bentonite Bnh Thun bin tnh s dng
l 0,5 mol% Pd.

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TP CH PHT TRIN KH&CN, TP 11, S 08 - 2008

chuyn ho (%)

100
80
60
40
20
0
0

15

30

45

60

Thi gian (pht)

Hnh 6. chuyn ha phn ng Heck trong iu kin c h tr ca vi sng (dung mi DMF, base l
Na2CO3, 0,5 mol% xc tc Pd, cng sut 800 W)

Kt qu nghin cu (Hnh 6) cho thy tc phn ng tng mt cch ng k so vi

trng hp gia nhit thng thng. chuyn ha ca phn ng t n 97% ch sau 1 gi
phn ng. Trong khi , phn ng trong iu kin gia nhit thng thng ch cho chuyn
ha 61,3% sau 6 gi phn ng vi cng mt hm lng xc tc (0,5 mol%), cng dung mi
(DMF) v cng base (Na2CO3). iu ny c th c gii thch da trn tc dng ca vi sng
trong iu kin s dng dung mi phn cc nh DMF. Cn lu cc phn t phn cc chu
nh hng ca vi sng nhiu hn. Cp nhit bng vi sng din ra trong lng dung dch v
ng nht hn, gip cho qu trnh phn ng cng nh cc qu trnh khuch tn, hp ph v
gii hp ph trn b mt xc tc din ra tt hn [14].
4. KT LUN
Tm li, nhm nghin cu chng ti iu ch xc tc bentonite Bnh thun bin tnh
theo phng php trao i cation vi dung dch PdCl2, vi hm lng Pd c trong xc tc l
0,14 mmol/g xc tc. Xc tc c b mt ring BET l 160,36 m2/g. Xc tc Pd iu ch c
c hot tnh cao trong phn ng ghp i Heck gia 4-iodotoluene v styrene, t c
chuyn ho 61,3% (trong t l sn phm trans-4-methylstilben: 1-phenyl-1-tolylethylene
vo khong 7,5:1) sau 6 gi phn ng vi iu kin: dung mi phn ng l DMF, hm lng
xc tc l 0,5 mol%, nhit phn ng l 120oC, base s dng l Na2CO3. Kt qu nghin cu
cn cho thy xc tc iu ch c c kh nng thu hi v ti s dng trong phn ng Heck.
Khi thc hin phn ng trong iu kin c s h tr ca vi sng, tc phn ng tng ln
ng k, chuyn ha t n 97% ch trong 1 gi phn ng, vi hm lng xc tc 0,5
mol%. Mc d y mi ch l nhng kt qu bc u nhng m ra trin vng s dng
bentonite Bnh Thun bin tnh lm xc tc cho cc phn ng ghp i xy dng b khung
carbon l cc phn ng quan trng ang c cc nh khoa hc trn th gii quan tm nhng
vn cha c nghin cu nhiu Vit Nam - v hng nghin cu ny cn c tip tc.

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Science & Technology Development, Vol 11, No.08 - 2008

MODIFIED BINH THUAN BENTONITE AS CATALYST FOR THE HECK

CROSS-COUPLING REACTION BETWEEN IODOTOLUENE
AND STYRENE
Phan Thanh Son Nam, Vuong Quang Thao
University of Technology, VNU-HCM
ABSTRACT: Modified Binh Thuan bentonite catalyst was prepared by exchanging with
aqueous solution of PdCl2, giving a catalyst loading of 0.14 mmol of Pd/g (AAS) and surface
areas of160.36 m2/g. The Pd2+ - exchanged bentonite effectively catalyzed the Heck carboncarbon cross-coupling reaction between 4-iodotoluene and styrene. The reaction was
performed using less than 1 mol% catalyst at 120oC in dimethylformamide (DMF) in the
presence of Na2CO3 as a base, affording the cross-coupling products in good conversions
(trans-4-methylstilben: 1-phenyl-1-tolylethylene = 7.5 : 1), identified by GC and GC-MS. The
catalyst could be facilely separated from the reaction mixture and could be reused in
subsequent reaction without significant degradation in activity. It was also observed that the
reaction rate was significantly enhanced under microwave irradiation.
Key words: bentonite, Heck reaction, 4-iodotoluene, styrene, palladium.
TI LIU THAM KHO
[1]. K. C. Nicolaou, Paul G. Bulger, and David Sarlah, Palladium-catalyzed crosscoupling reactions in total synthesis, Angewandte Chemie International Edition, 44,
4442-4489 (2005).
[2]. David H. Brown, Evaluation of kilogram-scale Sonogashira, Suzuki, and Heck
coupling routes to oncology candidate CP-724,714, Organic Process Chemical
Research & Development, 9, 440-450 (2005).
[3]. Lutz F. Tietze, Hiriyakkanavar IIa, and Hubertus P. Bell, Enantioselective palladiumcatalyzed transformations, Chemical Reviews, 104, 3453-3516 (2004).
[4]. Irina P. Beletskaya, and Andrei V. Cheprakov, The Heck reaction as a sharpening
stone of palladium catalysis, Chemical Reviews, 100, 3009-3066 (2000).
[5]. Nam T. S. Phan, Matthew Van Der Sluys, and Christopher W. Jones, On the nature of
the active species in palladium catalyzed Mizoroki-Heck and Suzuki-Miyaura couplings
homogeneous or heterogeneous catalysis, a critical review, Advanced Synthesis &
Catalysis, 348, 609-679 (2006).
[6]. Nguyn c Chu, Trng Minh Lng, Ng Th Thun, Phn ng ankyl ha toluen
bng isopropyl bromua trn xc tc bentonit Thun Hi bin tnh, Tp ch Ha hc,
35, 70-74 (1997).
[7]. Ng Th Thun, Hoa Hu Thu, Nguyn Vn Bnh, Trn Th Thu Nga, Tng hp v
c trng ca t st Thun Hi c chng bng cc polioxocation kim loi, Tp ch
Ha hc, 35, 29-33 (1997).
[8]. Trn Th Vit Hoa, Trn Hu Hi, Phan Thanh Sn Nam, Nghin cu phn ng alkyl
ha toluene trn xc tc bentonite bin tnh, Tp ch Pht trin Khoa hc & Cng ngh,
3, 64-71 (2000).

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TP CH PHT TRIN KH&CN, TP 11, S 08 - 2008

[9]. Nam T. S. Phan, David H. Brown, Harry Adams, Sharon E. Spey, and Peter Styring,
Solid-supported cross-coupling catalysts derived from homogeneous nickel and
palladium coordination complexes, Dalton Transactions, 1348-1357 (2004).
[10]. Phan Thanh Sn Nam, Bi Th Hng Hng, ng c Tu, Trn Th Thanh Tho,
Nghin cu s dng bentonite Bnh Thun bin tnh lm xc tc cho phn ng Heck
ca iodobenzene v styrene, Hi ngh Xc tc & Hp ph ton quc ln th IV, thng
8 nm 2007.
[11]. Rajender S. Varma, Kannan P. Naicker, Per J. Liesen, Palladium chloride and
tetraphenylphosphonium bromide intercalated clay as a new catalyst for the Heck
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