Diaryliodonium salts are catalytically carbonylated by CO generated in situ from chloroform and aqueous alkali in the presence of (Ph3P)2PdCl2 in good yields under N2 at 50 °C.
References
1.
ColquhounH. M., ThompsonO. J. and TwiggM. V., Carbonylation: Direct Synthesis of Carbonyl Compounds, Plenum Press, New York, 1991.
2.
GrushinV. V. and AlperH., Organometallics, 1993, 12, 3846.
3.
MoriartyR. M., EpaW. R. and AwasthiA. K., J. Am. Chem. Soc., 1991, 113, 6315; MoriartyR. M. and EpaW. R., Tetrahedron Lett., 1992, 33, 4095; HinkleR. J., PoulterG. T. and StangP. J., J. Am. Chem. Soc., 1993, 115, 11626; KangS. K., JungK. Y., ParkC. H. and JangS. B., Tetrahedron Lett., 1995, 36, 8047; KangS. K., LeeH. W., JangS. B., KimT. H. and PyunS. J., J. Org. Chem., 1996, 61, 2604; KangS. K., YamahuchiT., KimT. H. and HoP. S., J. Org. Chem., 1996, 61, 9082; KangS. K., LeeH. W., ChoiW. K., HongR. K. and KimJ. S., Synth. Commun., 1996, 26, 4219.
4.
Hypervalent Iodine in Synthesis XXVIII: The Preparation and Utilization of Polymer-Supported Phenyliodine(III) Diacetate, WangG. P. and ChenZ. C., Synth. Commun., 1999, in press.
5.
The Merck Index, 10th edn., no. 1093.
6.
The Merck Index, 10th edn., no. 9363.
7.
GilmanH., LanghamW. and WillisH. B., J. Am. Chem. Soc., 1940, 62, 346.
8.
EffenbergerF. and GleiterP., Chem. Ber., 1964, 97, 480.