Synthesis of β-Keto Esters by Carbonylation of Halomethylketones

A. L. Lapidus; O. L. Eliseev; T. N. Bondarenko; O. E. Sizan; A. G. Ostapenko; I. P. Beletskaya

doi:10.1055/s-2002-20027

SHORTPAPER

Synthesis of β-Keto Esters by Carbonylation of Halomethylketones

A. L. Lapidus*^a, O. L. Eliseev^a, T. N. Bondarenko^a, O. E. Sizan^a, A. G. Ostapenko^a, I. P. Beletskaya^b
^a N.D. Zelinsky Institute of Organic Chemistry RAS, Moscow, Russian Federation
Fax: +7(95)1355303; e-Mail: oleg@ioc.ac.ru;
^b Department of Chemistry, Moscow State University, Moscow, Russian Federation
Fax: +7(95)9381844; e-Mail: beletska@org.chem.msu.su;

Abstract

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Abstract

A number of β-keto esters were synthesized by Pd-catalyzed carbonylation of halomethylketones in the presence of tributylamine in 68-86% yields. The reaction is completed in 2 hours at 110 °C and 10 bar CO pressure. Chloromethylketones are carbonylated selectively while 2-bromoacetophenone is partly reduced to acetophenone as a byproduct. The reaction can be carried out at atmospheric pressure though the rate stays low. The reaction mechanism is discussed.

Key words

halomethylketones - β-keto esters - carbonylation - palladium - catalysis

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References

<A NAME="RE07501SS-1A">1a</A> Brown DJ. In Comprehensive Heterocyclic Chemistry Vol. 3: Katritzky AR. Rees CW. Pergamon; London: 1984. p.113

<A NAME="RE07501SS-1B">1b</A> Elguero J. In Comprehensive Heterocyclic Chemistry Vol. 5: Katritzky AR. Rees CW. Pergamon; London: 1984. p.277

<A NAME="RE07501SS-1C">1c</A> Lang SA. Lin Y.-i. In Comprehensive Heterocyclic Chemistry Vol. 6: Katritzky AR. Rees CW. Pergamon; London: 1984. p.61

<A NAME="RE07501SS-1D">1d</A> Brown DJ. In The Chemistry of Heterocyclic Compounds Vol. 16: Weissberger A. Wiley-Interscience; New York: 1962. p.48

<A NAME="RE07501SS-1E">1e</A> Wiley RH. Wiley P. In The Chemistry of Heterocyclic Compounds Vol. 20: Weissberger A. Wiley-Interscience; New York: 1964. p.9

<A NAME="RE07501SS-1F">1f</A> Wiley RH. Wiley P. In The Chemistry of Heterocyclic Compounds Vol. 20: Weissberger A. Wiley-Interscience; New York: 1964. p.13

<A NAME="RE07501SS-2A">2a</A> Benningshof JCJ. Blaauw RH. Van Ginkel AE. Rutjes FPJT. Fraanje J. Goubitz K. Schenk H. Hiemstra H. Chem. Commun. 2000, 1465

<A NAME="RE07501SS-2B">2b</A> Compernolle F. Baens N. Hoornaert GJ. Bull. Soc. Chim. Belg. 1997, 106: 433

<A NAME="RE07501SS-2C">2c</A> Coffey DS. Overman LE. Stappenbeck F. J. Am. Chem. Soc. 2000, 122: 4904

<A NAME="RE07501SS-2D">2d</A> Haudrechy A. Chassaing C. Riche C. Langlois Y. Tetrahedron 2000, 56: 3181

<A NAME="RE07501SS-2E">2e</A> Backhaus D. Tetrahedron Lett. 2000, 41: 2087

<A NAME="RE07501SS-3A">3a</A> Raboin J.-C. Beley M. Kirsch G. Tetrahedron Lett. 2000, 41: 1175

<A NAME="RE07501SS-3B">3b</A> Asuka M. inventors; Japanese Patent 08302286. ; Chem. Abstr. 1997, 126, 90788

<A NAME="RE07501SS-3C">3c</A> Sun S, Hadnagy TD, Davenport TE, Uchida H, Atsuki T, Uozumi G, Kegeyama K, and Ogi K. inventors; Eur. Pat. Appl. EP 950727. ; Chem. Abstr. 1999, 131, 294430

<A NAME="RE07501SS-3D">3d</A> Toth E. Van Uffelen I. Helm L. Morbach AE. Ladd D. Briley-Sæbø K. Kellar KE. Magn. Res. Chem. 1998, 36: S 125

<A NAME="RE07501SS-3E">3e</A> Matsuura H, and Nishio A. inventors; Japanese Patent 09318814. ; Chem. Abstr. 1998, 128, 55501

<A NAME="RE07501SS-3F">3f</A> Luitjes H, Van Haveren J, Frissen AE, Schmets GH, Frans FJML, Kroon EGA, and Van Der Waal JA. inventors; Eur. Pat. Appl. EP 881253. ; Chem. Abstr. 1999, 130, 39161

<A NAME="RE07501SS-3G">3g</A> Nishikawa M, Mutsuga Y, Yamamoto K, and Matsuki Y. inventors; Japanese Patent 1060275. ; Chem. Abstr. 1998, 128, 218109

<A NAME="RE07501SS-3H">3h</A> Hoeblel D. Reinerf T. Schmidt AJ. Sol-Gel Technol. 1997, 10: 115 ; Chem. Abstr. 1998, 128, 83606

<A NAME="RE07501SS-4">4</A> Hauser CR. Hudson BE. Org. React. 1942, 1: 266

<A NAME="RE07501SS-5A">5a</A> Krapcho AP. Diamanti J. Cayen C. Bingham R. Org. Synth. 1967, 47: 20

<A NAME="RE07501SS-5B">5b</A> Snyder HR. Brooks LA. Shapiro SH. Org. Synth. Coll. Vol. 2 Wiley; New York: 1943. p.531

<A NAME="RE07501SS-6A">6a</A> Bestmann HJ. Kolm H. Chem. Ber. 1963, 96: 1948

<A NAME="RE07501SS-6B">6b</A> Rathke MW. Sullivan DF. Tetrahedron Lett. 1973, 1297

<A NAME="RE07501SS-6C">6c</A> Sicher J. Sipos F. Tichi M. Coll. Czech. Chem. Commun. 1961, 26: 847

<A NAME="RE07501SS-6D">6d</A> Spencer TA. Weaver TD. Villarica RM. Friary RJ. Posler J. Schwartz MA. J. Org. Chem. 1968, 33: 712

<A NAME="RE07501SS-6E">6e</A> Stiles M. J. Am. Chem. Soc. 1959, 81: 2598

<A NAME="RE07501SS-6F">6f</A> Stork G. Brizzolara A. Landesman H. Szmuszkovich J. Terrell R. J. Am. Chem. Soc. 1963, 85: 207

<A NAME="RE07501SS-6G">6g</A> Lawesson SO. Gonwall S. Sandberg R. Org. Synth. 1962, 42: 28

<A NAME="RE07501SS-6H">6h</A> Moriconi EJ. White JG. Franck RW. Jansing J. Kelly JF. Salomone RA. Shimakawa Y. Tetrahedron Lett. 1970, 27

<A NAME="RE07501SS-7A">7a</A> Colguhoun HM. Thompson DJ. Twigg MV. Carbonylation. Direct Synthesis of Carbonyl Compounds Plenum Press; New York: 1991.

<A NAME="RE07501SS-7B">7b</A> Parshall GW. Itell SD. Homogeneous Catalysis, The Applications and Chemistry of Catalysis by Soluble Transition Metal Complexes Wiley-Interscience; New York: 1992. 2nd ed.

<A NAME="RE07501SS-7C">7c</A> Gulevich YuV. Bumagin NA. Beletskaya IP. Russ. Chem. Rev. 1988, 57: 299

<A NAME="RE07501SS-7D">7d</A> Lapidus AL. Pirozhkov SD. Russ. Chem. Rev. 1989, 58: 117

<A NAME="RE07501SS-8">8</A> Stille K. Wong PK. J. Org. Chem. 1975, 40: 532

<A NAME="RE07501SS-9">9</A> Choudary BM. Reddy NP. Jamil MZ. Polyhedron 1986, 5: 911

<A NAME="RE07501SS-10">10</A> Adapa SR. Pasad CSN. J. Chem. Soc., Perkin Trans. 1 1989, 1706

<A NAME="RE07501SS-11">11</A> Cavinato G. Toniolo L. J. Mol. Catal. A: Chem. 1999, 143: 325

<A NAME="RE07501SS-12A">12a</A> Heck RF. Adv. Catal. 1977, 26: 323

<A NAME="RE07501SS-12B">12b</A> Schoenberg A. Bartoletti I. Heck RF. J. Org. Chem. 1974, 39: 3318

<A NAME="RE07501SS-13">13</A> Hidai M. Kokura M. Uchida Y. J. Organomet. Chem. 1973, 52: 431

<A NAME="RE07501SS-14">14</A> Moser RW. Wong AW. Kildahl NK. J. Am. Chem. Soc. 1988, 110: 2816

<A NAME="RE07501SS-15">15</A> Cassar L. Foà M. Gardano A. J. Organomet. Chem. 1976, 121: C55

<A NAME="RE07501SS-16">16</A> Alper H. Hashem K. Heveling J. Organometallics 1982, 1: 775

<A NAME="RE07501SS-17">17</A> Gore PH. Chem. Rev. 1955, 55: 229