Cyclic Triolborate
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Suzuki-Miyaura coupling reaction is carried out typically in the presence of a base and often in the
coexistence of water as many boronic acids convert to cyclic anhydrides by dehydrotrimerization.
However, since some boronic acids are hydrolyzed in basic aqueous solution, a large excess of boronic
acids are often required.
Organic cyclid-triolborate salts are the ate complexed borate reagents developed by Miyaura, et al.
There is no need to add bases in cross coupling reactions catalyzed by palladium. They may be used
in aqueous and nonaqueous systems. They are also useful in N-arylation reaction with copper
catalysts.
Reactions:
Suzuki-Miyaura Cross Coupling Reactions with Triolborate
X
Br
Br
Br
Br
Br
Br
Br
Br
FG
4−NO2
4−COMe
4−CO2Me
4−CI
2−MeO
4−MeO
4−MeO
4−NMe2
t[h]
5
5
5
5
5
5
22
22
Yield[%]
99
99
99
99
98
97
89
92
Angew. Chem. Int. Ed., 47, 928-931 (2008).
Suzuki-Miyaura Cross Coupling Reactions using heterocyclic triolborates
Ar1
Ar2
M
t[h]/T[°C]
Yield[%]
Li
22/80
901)
Li
22/80
751)
Li
22/80
701)
Na
10/100
86
K
10/100
88
Angew. Chem. Int. Ed., 47, 928-931 (2008).
Suzuki-Miyaura Cross Coupling Reactions using heterocyclic triolborates
Ar
FG
t[h]/T[°C]
Yield[%]
MeO
3/rt.
quant.
MeO
4/rt.
99
MeO
5/rt.
94
MeO
5/rt.
92
MeO
5/rt.
quant.
MeO
6/rt.
99
MeO
5/rt.
95
MeO
5/rt.
quant.
MeO
5/rt.
quant.
Ar
FG
t[h]/T[°C]
Yield[%]
NO2
10/80
99
MeO
7/rt.
95
MeO
5/rt.
98
MeO
5/rt.
quant.
MeO
5/rt.
quant.
MeO
5/rt.
98
MeO
5/rt.
98
NO2
5/100
98
Product List
Product List (Continued)
Besides above products, Wako provides over 30 kinds of cyclic
triolborates. Search the website www.e-reagent.com using
"triolborate" as a keyword.Please feel free to contact us
if you want to order other package sizes.