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1
TETRABUTYLAMMONIUM BROMIDE
Tetrabutylammonium Bromide
1
S
SMe
MeI, KOH
(1)
Bu
4
NBr
85%
N
H
N
n
-Bu
4
NBr
[1643-19-2]
C
16
H
36
BrN (MW 322.43)
InChI = 1/C16H36N.BrH/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-
12-8-4;/h5-16H2,1-4H3;1H/q+1;/p-1/fC16H36N.Br/
h;1h/qm;-1
InChIKey = JRMUNVKIHCOMHV-SLKHSEMMCI
O
O
Bu
4
NBr cat
(2)
O
OK
toluene, 90 °C, 3 h
95%
Br
Bu
4
NBr is also very effective in promoting nucleophilic aro-
matic substitution reactions to produce aryl thio esters,
15
aryl
ethers,
16
and
N
-arylbenzodiazepines.
17
Some glycosylations were
shown to be efficient only in the presence of Bu
4
NBr.
18
(phase-transfer catalyst;
1
source of nucleophilic bromide;
1
addi-
tive in transition metal catalyzed carbon–carbon bond-forming
reactions;
31
ionic liquid solvent
32
)
Alternate Name:
TBAB.
Physical Data:
mp 103–104
◦
C.
Solubility:
sol H
2
O, 1% aq NaOH, CH
2
Cl
2
, EtOH; slightly sol
toluene; insol 20% aq NaOH.
Form Supplied in:
anhydrous white solid.
Analysis of Reagent Purity:
tetraalkylammonium salts can be
titrated with potassium 3,5-di-
t
-butyl-2-hydroxybenzenesulfo-
nate and iron(III) chloride.
1a
Preparative Methods:
several methods are available to recover
the quaternary ammonium ion efficiently.
1a
Prepared by reac-
tion of tri-
n
-butylamine and
n
-butyl bromide.
1a
Purification:
all manipulations should be carried out in a dry-
box. The salt can be crystallized from benzene (5 mL g
−
1
)at
80
◦
C by adding 3 vol of hot hexane and allowing to cool. It can
also be purified by precipitation of a saturated solution in dry
CCl
4
by addition of cyclohexane or by crystallization from a
mixture CH
2
Cl
2
–Et
2
O. After filtration, the solid is further dried
by heating at 75
◦
C under vacuo (0.1 mmHg) in the presence of
P
2
O
5
.
2
Handling, Storage, and Precautions:
stable, highly hygroscopic;
if used in a reaction requiring anhydrous conditions, it should
be manipulated in a glove-bag or in a dry-box. Protect from
moisture. Harmful by inhalation or ingestion.
Catalyst for Oxidation Reactions.
Phase-transfer oxidation
of alcohols to acids,
19
alkenes to carboxylic acids,
18
sulfides to
sulfones,
20
and sulfilimines to sulfoximines
21
have also been car-
ried out in the presence of tetrabutylammonium bromide along
with an oxidizing reagent.
Catalyst for C–C Bond Formation.
The presence of Bu
4
NBr
was shown to be essential in a number of carbon–carbon bond-
forming reactions, such as the alkylation of allyl sulfones
22
and of
MALONONITRILE
,
23
and in the lead-promoted Barbier-type reaction
of propargyl bromide with aldehydes.
24
It has also been used in
the efficient synthesis of racemic -alkyl and ,-dialkyl -amino
acids by phase-transfer alkylation of Schiff bases (eq 3).
25
O
1. BuBr, K
2
CO
3
, Bu
4
NBr
MeCN
O
OMe
H
2
N
(3)
OH
N
p
-ClC
6
H
4
2. hydrolysis
75%
Bu
p
-ClC
6
H
4
The presence of Bu
4
NBr was shown to be necessary to increase
the efficiency of some carbon–carbon double bond forming re-
actions such as Heck-type couplings,
26
dehydrohalogenations,
27
and Horner–Emmons–Wittig reactions.
28
Original Commentary
Alkyl and Alkenyl Bromides.
Bu
4
NBr can be used as a pow-
erful source of bromide for nucleophilic displacement reactions
of triflates
29
André B. Charette
Université de Montréal, Montréal, Québec, Canada
and iodonium salts.
30
Catalyst for C–X Bond Formation.
Tetrabutylammonium
bromide is undoubtedly one of the most widely used phase-
transfer catalysts. It combines the lipophilicity required for an effi-
cient phase-transfer catalyst with the hydrophilicity necessary for
efficient catalyst recovery. It has been successfully used in the
liquid–liquid or solid–liquid phase-transfer alkylation of the
NH groups of anilines,
3
amides,
4
lactams,
5
sulfonamides,
6
and
other nitrogen heterocyclic compounds.
7
Sulfur
8
and oxygen-
containing functional groups
9
can also be smoothly alkylated un-
der phase-transfer conditions. Several
S
-alkylthioacridines have
been prepared by liquid–liquid
10
or solid–liquid
11
phase-transfer
catalysis (eq 1).
Carboxylic acids
12
and phenols
13
can also be alkylated in the
presence of tetrabutylammonium bromide. Macrolides can be syn-
thesized by an intramolecular S
N
2 reaction of a bromo ester via
simulated high dilution conditions (eq 2).
14
First Update
Rafael Chinchilla & Carmen Nájera
Universidad de Alicante, Alicante, Spain
Phase-transfer Catalyst.
TBAB is one of the most common
phase-transfer (PT) catalysts, being employed in numerous C–C,
C–N, C–O, C–S, and C–P bond forming reactions performed
under liquid–liquid and liquid–solid phase-transfer catalysis
(PTC) conditions, as well as in halogenation and oxidation
reactions.
33
Substrates bearing acidic C–H hydrogens, easily removed
under rather mild basic PTC conditions, are appropriate for
C
-alkylation reactions using TBAB as PT catalyst.
p
-Chlorophe-
Avoid Skin Contact with All Reagents
2
TETRABUTYLAMMONIUM BROMIDE
nylacetonitrile is
-alkylated in the presence of TBAB un-
der solid–liquid PTC conditions,
34
whereas 4-halobutyronitriles
cyclizes to the corresponding cyclopropanes using a similar
procedure.
35
Iminic derivatives of
-amino acids such as glycine
36
as well as cyclic derivatives of serine
37
are suitable substrates for
alkylation reactions using TBAB under PTC conditions, driving to
racemic mixtures of -amino acid derivatives. When chiral deriva-
tives are used as starting materials, diastereoselectively enriched
C
-alkylated compounds are obtained, leading to the asymmetric
synthesis of amino acids. Chiral derivatives of glycine,
38
alanine
39
(eq 4),
39a
or serine,
40
as well as peptides,
41
are employed in these
TBAB-promoted asymmetric alkylation reactions. Phosphonate
equivalents of iminic glycinates react with acrylates in a Michael
addition fashion under liquid–liquid PTC conditions in the pres-
ence of TBAB.
42
in the coordination of the bromide anion of TBAB to neutral
tin(IV) enolates, thus forming highly coordinated tin enolates
with a marked change in chemoselectivity, showing low nucle-
ophilicity toward carbonyl moieties and higher nucleophilicity
to organic halides,
49a
or high reactivity in Michael additions to
,
-unsaturated esters.
49b
Imidazoles are
N
-alkylated at the 1-position using alkyl halides,
an organic
50a
or aqueous inorganic base,
50b
and a catalytic amount
of TBAB, conditions also suitable for the
N
-alkylation of carba-
zoles
51
or quinoxalinones.
52
Acridones are fast and efficiently
N
-alkylated when reacted with alkyl halides in a mixture of
sodium hydroxide and potassium absorbed in alumina, in the
presence of TBAB under microwave irradiation (eq 7).
53
The PTC
conditions using TBAB as catalyst are used for the
N
-alkylation
of sulfoximines,
54
N
-diethoxyphosphoryl-
O
-benzylhydroxy-
lamine
55
or amides, and lactams. In this last case solvent-free
conditions and microwave irradiation accelerate considerably the
reaction.
56
The aziridination of -bromo-2-cyclopenten-2-one
is performed using primary amines in water in the presence of
TBAB (eq 8).
57
Me
Me
OO
OO
HC
CCH
2
Br
Me
Me
(4)
Me
TBAB
K
2
CO
3
, MeCN, rt
Ph
N
Ph
N
Me
70% (98:2 dr)
O
Aldehydes and ketones are alkynylated under liquid–liquid
PTC conditions at room temperature yielding propargylic alco-
hols (eq 5), best results being obtained for aliphatic ketones and
nonenolizable aldehydes.
43
n
-C
3
H
7
Br
TBAB
N
H
NaOH, K
2
CO
3
, Al
2
O
3
, MW
O
HO
Ph
O
(7)
Ph
(5)
N
TBAB
PhF, aq NaOH, rt
Me
88%
88%
The use of TBAB as phase-transfer catalyst can be very
effective in the creation of C–C bonds by using organometallic
compounds that tolerate aqueous media. Tin in the presence of
allyl bromides can be used for the allylation of aldehydes un-
der Barbier conditions in water as solvent when using TBAB
as catalyst.
44
Aldehydes are allylated using potassium allyl- and
crotyltrifluoroborates in aqueous dichloromethane, the presence
of TBAB significantly accelerating the reaction.
45
Samarium in
the presence of allyl bromide can be used for the allylation of
aldonitrones and hydrazones in aq DMF when TBAB is emp-
loyed as an additive,
46
a reaction which can also be performed
using gallium or bismuth.
47
Epoxides are coupled to allyl halides
using gallium or samarium in aqueous media in the presence of a
catalytic amount of TBAB to give homoallylic alcohols via pre-
liminary epoxide rearrangement to the corresponding aldehyde
(eq 6).
48
O
O
PhCH
2
NH
2
Br
(8)
Ph
TBAB, H
2
O, rt
N
98%
Alcohols can be alkylated in the presence of TBAB under
liquid–liquid PTC conditions and an aqueous inorganic base.
58
The procedure is more easily performed when phenols are
employed,
59
allowing solid–liquid
60
and solventless
61
PTC re-
action conditions. Monoesters of 1,2-diols are obtained from ben-
zoic acid derivatives and epoxides by adding a catalytic amount
of TBAB, the reaction not only involving a PT mechanism but
also a stabilization of the dissociation of the benzoic acid and
generation of hydrogen bromide which induces epoxide opening
(eq 9).
62
Carbonates are also obtained from chloroformates and
phenols under solid–liquid PTC in the presence of TBAB.
63
Br
O
O
O
Ph
CHO
Ph
Sm, TBAB
DMF-H
2
O, rt
O
O
OH
O
TBAB
(6)
+
Ph
OPh
MeCN, 80
°C
HO
OH
O
76%
O
OPh
(9)
The role of TBAB in some of these reactions probably is
not only that of phase-transfer catalyst, but also to activate the
formed allylmetal reagents, as it is known that organolead com-
pounds are activated with TBAB.
24
This activation ability is shown
OH
HO
92%
A list of General Abbreviations appears on the front Endpapers
3
TETRABUTYLAMMONIUM BROMIDE
The
S
-alkylation of 4-mercapto-6-methyl-2-pyrone with allyl
and propargyl halides is performed using TBAB as PT agent
in chloroform-aqueous sodium hydroxide at room temperature
(eq 10),
64
whereas the double alkylation of sodium sulfide can be
carried out by mixing it with an alkyl halide under PTC conditions
in a water–toluene mixture.
65
using 2-iodoxybenzoic acid in the presence of TBAB under PTC
conditions (eq 13).
73
OH
PhI(OAc)
2
OH
TBAB
CH
2
Cl
2
, H
2
O, rt
O
OH
Cl
CHO
(13)
Me
SH
+
OH
TBAB
+
O
CHCl
3
, aq NaOH
70%
3%
O
OH
Methyl aryl ketones are converted into benzoic acids by using
molecular oxygen and a catalytic amount of 1,3-dinitrobenzene
under basic PTC reaction conditions promoted by TBAB.
74
Cat-
alytic asymmetric epoxidation of
trans
-chalcone is achieved using
basic hydrogen peroxide and poly-
L
-Leu as catalyst, the addition
of TBAB significantly accelerating the reaction.
75
Me
S
O
(10)
O
OH
65%
Source of Bromide.
The use of TBAB as a source of the bro-
mide anion allows the regioselective ring opening of epoxides to
bromohydrins at room temperature when magnesium(II) nitrate
is used as catalyst, the bromide attack taking place at the less-
hindered position of the epoxide (eq 14).
76
This type of TBAB-
promoted epoxide ring opening gives rise to five-membered cyclic
orthoesters when performed in the presence of perfluorocarboxy-
lates.
77
Cyclic sulfates from chiral 2,3-diol esters can also be re-
gioselectively ring opened to bromohydrins for the synthesis of
chiral
,
-epoxy esters.
78
The
P
-alkylation of phosphane boranes can be carried out in
an inorganic base-containing biphasic solution in the presence of
TBAB as PT catalyst, which allows the synthesis of polydentate
phosphane ligands in much higher yields than when using the
n
-butyllithium-promoted standard conditions (eq 11).
66
BH
3
BH
3
P
Br
P
Ph
H
Ph
t
-Bu
t
-Bu
(11)
TBAB
Ph
aq KOH, PhMe, rt
Mg(NO
3
)
2
, TBAB
t
-Bu
Br
P
Br
(14)
O
CHCl
3
, rt
BH
3
OH
87%
93%
The monochlorination of cubane has been achieved using
carbon tetrachloride in 50% aqueous sodium hydroxide in the
presence of TBAB under PTC conditions,
67
the reaction probably
involving SET from the hydroxide to carbon tetrachloride (eq 12).
Chlorination of 2,3,5,6-tetrachloropyridine to pentachloropyri-
dine can be achieved via carbanionic intermediates using chlo-
roform or hexachloroethane in aqueous sodium hydroxide in the
presence of TBAB.
68a
These reaction conditions can also be
employed for the preparation of 3,3-dichlorobenzosultams.
68b
Hydroxyheteroarenes can be brominated by using a combi-
nation of phosphorus pentoxide and TBAB,
79
whereas diethyl
-hydroxyphosphonates can be transformed into the correspond-
ing -brominated derivatives by using a neutral system formed by
triphenylphosphane and 2,3-dichloro-5,6-dicyanobenzoquinone
(DDQ) in the presence of TBAB.
80
Additive in Transition Metal-catalyzed C–C Bond-forma-
tion Reactions.
The addition of tetraalkylammonium salts fre-
quently enhances the rate of transition-metal-catalyzed (mainly
palladium) cross-coupling reactions, such as the Heck coupling,
81
especially in aqueous solvents. Their effect cannot only be con-
sidered as a consequence of the typical phase-transfer activity,
but also as a stabilization of nano-sized metal colloids that can
be formed by reduction of the added metal source, the surfactant
preventing undesired agglomeration to unreactive species such as
palladium black by forming a monomolecular layer around the
metal core.
82
Thus, TBAB has been used as an additive in Heck
cross-coupling reactions under ligand-free palladium catalysis
83
even in neat water
84
(eq 15), or using
N
-heterocyclic carbene pal-
ladium complexes
85
or CN-palladacycles
86
as palladium sources.
Cl
CCl
4
, 50% NaOH
TBAB, rt
(12)
81%
Benzylic carbons and the tertiary carbons in adamantanes are
oxidized to alcohols and/or ketones by using molecular oxygen,
N
-hydroxyphthalimide as radical initiator, and TBAB.
69
Benzylic
and allylic alcohols are oxidized to the corresponding aldehydes
or ketones by using
tert
-butyl hydroperoxide in the presence of
catalytic amounts of copper salts and TBAB as PT catalysts.
70
Oxone
R
in the presence of a manganese(III) complex as catalyst
oxidizes secondary and benzylic alcohols to the corresponding
carbonyl compounds under TBAB-promoted liquid–liquid PTC
conditions,
71
whereas
m
-CPBA is employed for the oxidation of
alcohols in the presence of a catalytic amount of TEMPO and
TBAB.
72
Pd(OAc)
2
, TBAB
NaHCO
3
, H
2
O
80–90
°C
Ph
PhI
+
(15)
CN
CN
81%
The addition of TBAB has also shown to enhance the rate of
the palladium-catalyzed Suzuki cross-coupling reaction between
Selective oxidation of secondary alcohols is achieved
Avoid Skin Contact with All Reagents
4
TETRABUTYLAMMONIUM BROMIDE
an aryl halide and an arylboronic acid [ArB(OH)
2
] in aqueous
solvents, not only by facilitating the solvation of the organic
substrates and by stabilization of palladium nanoparticles, but
also by the formation of [ArB(OH)
3
]
−
[
n
-Bu
4
N]
+
. Thus, when
palladium(II) acetate is used as catalysts, TBAB accelerates the
cross-coupling of iodoarenes,
87
bromoarenes,
87
chloroarenes,
88
bromothiophenes,
89
and -chloroacroleins
90
(eq 16) in water, or
the coupling of bromo or chloroarenes when using poly(ethylene
glycol-400) as solvent.
91
Oxime-derived palladacycles can be
used as catalysts in the presence of TBAB in the Suzuki coupling
of chloroarenes in water (eq 17),
92
as well as di(2-pyridyl)methyl-
amine-palladium dichloride complexes.
93
using the combination of palladium(II) acetate and TBAB in aq
DMF,
99
as well as employing palladium on charcoal as palladium
source and formate as reducing agent, in the presence of TBAB.
100
NHCONHCy
N
N
Pd
I
Cl
Cl
+
Ph
TBAB, pyrrolidine,
H
2
O, 100
°C
NHAc
Ph
Cl
(18)
CHO
Pd(OAc)
2
, TBAB
K
2
CO
3
, H
2
O, 45
°C
NHAc
+
B(OH)
2
S
90%
S
4
-ClC
6
H
4
(16)
CHO
Si(OEt)
3
N
OH
Pd
Cl
Cl
2
69%
Br
+
TBAB, aq 50 % NaOH
120
°C
N
Me
(19)
Me
Me
N
N
OH
B(OH)
2
100%
Pd
HO
Cl
2
TBAB, K
2
CO
3
H
2
O, 100
°C
Cl
+
CN
Me
Ionic Liquid Solvent.
Although the melting point of TBAB
is slightly higher than 100
◦
C, which is the border tempera-
ture for considering a salt as an ionic liquid and not simply a
molten salt,
32
its melting temperature drops when other reagents
are present; TBAB is therefore considered as an ionic liquid
with all the recyclability advantages of such solvents.
32
Molten
TBAB has been used as a solvent in the Michael addition of
thiols to electron-deficient olefins,
101
the bismuth(III)-catalyzed
ring opening of epoxides with anilines,
102
the monobromination
with
N
-bromosuccinimide of activated aromatics and heteroaro-
matics,
103
the cyclic carbonate formation from carbon dioxide and
oxiranes,
104
and the transthioacetalisation of acetals.
105
The advantages of ionic liquids added to its transition metal
nanoparticle stabilization ability, make molten TBAB applica-
ble as solvent in cross-coupling reactions such as the palladium-
catalyzed Heck reaction of aryl chlorides,
106
,
107c
bromides,
107
or
iodides;
108
the arylation of allylic alcohols,
109
and the synthesis
of 4-arylated coumarins from
o
-hydroxycinnamates by a domino
Heck reaction/cyclization process (eq 20).
110
Nanoparticles cre-
ated by reduction of palladium salts in nanoparticle-stabilizing
molten TBAB can be used for the Suzuki cross-coupling re-
actions of aryl bromides or chlorides,
111
the carbonylation of
aryl halides,
112
and the hydrogenolysis-free hydrogenation of
olefins.
113
Benzylic alcohols are dehydrogenated to the corre-
sponding ketones in molten TBAB with a catalytic amount of
palladium(II) chloride and a flow of argon.
114
Me
(17)
CN
69%
Recoverable nickel(0) metal colloids stabilized by the addi-
tion of TBAB catalyze the Suzuki coupling of aryl iodides and
bromides with organoboronic acids using ethanol as solvent, the
addition of triphenylphosphane being required when coupling
activated aryl chlorides.
94
The addition of TBAB can promote the palladium-catalyzed
Sonogashira coupling of aryl- or vinyl halides and terminal
alkynes when using palladium(II) acetate as palladium source in
ethanol as solvent
95
or palladium(II) chloride in water.
96
The use
of TBAB as an additive has found to be particularly important
when palladium-phosphinous acids
97
and di(2-pyridyl)methyl-
amine-palladium dichloride complexes
96a
(eq 18), even supported
on a polymer,
96b
have been used as catalysts in water as solvent.
The use of TBAB as additive allows the solvent-less sodium
hydroxide-promoted palladium-catalyzed Hiyama cross-coupling
reaction of deactivated aryl bromides or -chlorides and arylsilox-
anes, when palladium(II) acetate or a oxime-derived palladacycle
(eq 19) are used as palladium sources.
98
The homocoupling of
brominated or iodinated arenes to biaryls can be performed by
A list of General Abbreviations appears on the front Endpapers
5
TETRABUTYLAMMONIUM BROMIDE
O
21.
With NaClO: Akutagawa, K.; Furukawa, N.,
J. Org. Chem.
1984
,
49
,
2282.
MeO
Br
OMe
22.
Jonczyk, A.; Radwan-Pytlewski, T.,
J. Org. Chem.
1983
,
48
, 910.
Pd(OAc)
2
,
n
-Bu
4
NOAc
TBAB, 100
°C
23.
Diez-Barra, E.; de la Hoz, A.; Moreno, A.; Sanchez-Verdu, P.,
J. Chem.
Soc., Perkin Trans. 1
1991
, 2589.
OH
OMe
OMe
24.
Tanaka, H.; Hamatani, T.; Yamashita, S.; Torii, S.,
Chem. Lett.
1986
,
1461.
25.
O’Donnell, M. J.; Wojciechowski, K.; Ghosez, L.; Navarro, M.;
Sainte, F.; Antoine, J.-P.,
Synthesis
1984
, 313.
(20)
26.
Carlström, A.-S.; Frejd, T.,
Acta Chem. Scand.
1992
,
46
, 163.
27.
Makosza, M.; Lasek, W.,
Tetrahedron
1991
,
47
, 2843.
OH
CO
2
Me
28.
Texier-Boullet, F.; Foucaud, A.,
Tetrahedron Lett.
1980
,
21
, 2161.
OO
29.
(a) Binkley, R. W.; Ambrose, M. G.; Hehemann, D. G.,
J. Org. Chem.
1980
,
45
, 4387. (b) Ireland, R. E.; Häbich, D.; Norbeck, D. W.,
J. Am.
Chem. Soc.
1985
,
107
, 3271.
82%
30.
(a) Ochiai, M.; Oshima, K.; Masaki, Y.,
J. Am. Chem. Soc.
1991
,
113
,
7059. (b) Ochiai, M.; Oshima, K.; Masaki, Y.,
Tetrahedron Lett.
1991
,
32
, 7711.
1.
(a) Sjöberg, K.,
Aldrichim. Acta
1980
,
13
, 55. (b) Jones, R. A.,
Aldrichim. Acta
1976
,
9
, 35. (c) Weber, W. P.; Gokel, G. W.
Phase
Transfer Catalysis in Organic Synthesis
; Springer: New York, 1977.
(d) Starks, C. M.; Liotta, C.
Phase Transfer Catalysis
; Academic:
New York, 1978. (e) Dehmlow, E. V.; Dehmlow, S. S.
Phase Transfer
Catalysis
; Verlag Chemie: Deerfield Beach, FL, 1980. (f) Loupy, A.;
Tchoubar, B.
Salt Effects in Organic and Organometallic Chemistry
;
VCH: Weinheim, 1992.
31.
(a)
Handbook of Organopalladium Chemistry for Organic Synthesis
;
Negishi, E.; de Meijere, A. (Eds.); Wiley-Interscience: New York, 2002.
(b)
Metal-Catalyzed Cross-Coupling Reactions
2nd ed. Diederich,
F.; de Meijere, A. (Eds.); Wiley-VCH: Weinheim, 2004. (c)
Transition Metals for Organic Synthesis Building Block Fine Chemicals
2nd
ed.
Bolm,
C.;
Beller,
M.
(Eds.);
Wiley-VCH:
Weinheim,
2.
Perrin, D. D.; Armarego, W. L.
Purification of Laboratory Chemicals
;
3rd ed.; Pergamon: Oxford, 1988.
2004.
32.
(a) Welton, T.,
Chem. Rev.
1999
,
99
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