Chemistry Reference
In-Depth Information
O
Pd(OAc)
2
(0.5 mol%)
BuPAd
2
(1.5 mol %)
TMEDA, toluene
CO (2 .5-5 bar ), 80-120 °C
Br
B(OH)
2
23 examples
60 -89%
R
R'
R
R'
Scheme 10.65 Pd-catalysed carbonylative Suzuki reaction of aryl bromides.
O
B(OH)
2
Pd (PPh
3
)
4
(5 mol%)
NMP, CO ( 1 bar ), 60 °C
13 examples
52 -92%
Ar
3
Sb (OAc)
2
Ar
R'
R'
Scheme 10.66 Pd-catalysed
carbonylative
coupling
of
triarylantimony
dicarboxylates.
O
I
Pd(OAc)
2
, PPh
3
Na
2
CO
3
,THF,80 °C
CO (5 bar)
9examples
39-78%
BF
3
K
R
R
Scheme 10.67 Pd-catalysed carbonylative synthesis of aryl vinyl ketones.
O
I
Pd(tmhd)
2
(2 mol%)
K
2
CO
3
, 80 °C, anisole
CO (8 bar), 6 h
B(O H)
2
19 examples
70-96 %
R
R'
R
R'
Scheme 10.68 Pd(tmhd)
2
-catalysed carbonylative coupling of aryl iodides.
Kurita and co-workers described a carbonylative coupling of triar-
ylantimony dicarboxylates with arylboronic acids (Scheme 10.66).
81
Re-
markably, no base was needed in this system.
In 2009, Castanet and co-workers reported a useful protocol for aryl vinyl
ketone synthesis.
82
The carbonylative cross-coupling of potassium vinyltri-
fluoroborate or 2,3,6-trivinylcycloboroxane with aryl iodides affords vinyl
ketones in moderate yields (Scheme 10.67). This reaction is strongly influ-
enced by the substituents: whereas activated and ortho-substituted aryl
iodides gave low yields, good yields were achieved in the case of electron-
donating decorated aryl iodides.
In 2009, Cai and co-workers reported the use of an MCM-41-supported
bidentate phosphine-palladium(0) complex as catalyst for the carbonylative
Suzuki coupling of aryl iodides with arylboronic acids.
83
Pd(tmhd)
2
(thmd
¼
2,2,6,6-tetramethyl-3,5-heptanedionate) as another
catalyst for carbonylative coupling of aryl iodides with arylboronic acids was
reported by Bhanage and co-workers (Scheme 10.68).
84
The diketone (tmhd)
can act as ligand in this methodology and no additional ligand is required.
Pontikis and co-workers reported a convenient one-pot procedure for the
synthesis of 2-aroylindoles.
85
Using a domino palladium-catalysed CN
coupling-carbonylation-CC coupling
sequence,
2-aroylindoles were
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