Negishi E. 2002 Handbook of organopalladium chemistry for organic synthesis / 0635 647

				III.2.12.1 CROSS-COUPLING WITH ACYL HALIDES						645
				PdCl2(PhCN)2 (4 mol %)		Me2ClSi				Ph
				Et3N (0.1 equiv), toluene, r.t., 2 h
							O
	[52]
Ph			Cl				86%
SiMe2 +
	O
				PdCl2(PhCN)2 (4 mol %)		O	Ph
						Me2Si
			Et3N (2 equiv), toluene, 80 °C, 4 h
	[52]
							97%
				Scheme 14

due to the ease of disproportionation of trialkylchloroleads to tetraalkylleads and dialkyldichloroleads.

Triphenylbismuth can also be utilized for the coupling reaction (Scheme 15).[54] All three phenyl groups on bismuth can be used, since disproportionation of the intermediary dialkylchloroand alkyldichlorobismuth is fast.

Siloxycyclopropanes are considered as homoenolate equivalents and also undergo the coupling reaction with acyl halides to produce 1,4-dicarbonyl compounds (Scheme 16).[55]

Ph

Cl

Pd(PPh3)4 (1 mol %)

Et

Ph

Et4Pb +

THF, 65 °C, 3 h

(0.6 equiv)

O

O

[53]

84%

Me

Me

n-Bu4Pb +

Pd(PPh3)4 (1 mol %)

Me

Cl

n-Bu

Me

THF, 65 °C, 4 h

(0.6 equiv)

[53]

O

O

72%

Ph3Bi +

Me

Cl

Pd(OAc)2

(5 mol %)

Ph

Me

HMPA, 65 °C, 5 h

O

O

(excess)

[54]

92%

Scheme 15

Cl

PdCl2(PPh3)2

O

Cl

OSiMe3

Cl

(5 mol %)

OEt

+

EtO

CHCl3,

Me

O

90 −100 °C

Me

O

93%

[55]

Scheme 16

646	III Pd-CATALYZED CROSS-COUPLING

F.SUMMARY

1.Palladium-catalyzed coupling reactions of organozinc compounds with acyl halides are the fastest and mildest among the known methods using a variety of organometallic compounds.

2.Since organotin compounds are stable to water and oxygen, the method has widely been utilized for the synthesis of various compounds although the reaction requires a long time and high temperature.

3.Organometallic compounds, such as organomercury, boron, aluminum, zirconium, copper, silane, lead, and bismuth, can also be utilized for the coupling reactions, although these methods have not been studied extensively.

REFERENCES

[1]D. A. Shirley, Org. React., 1954, 8, 28.

[2]H. Reinheckel, K. Haage, and D. Jahnke, Organomet. Chem. Rev. A, 1969, 4, 47–136.

[3]G. H. Posner, Org. React., 1975, 22, 253–400.

[4]J. P. Collman, Acc. Chem. Res., 1975, 8, 342.

[5]E. Negishi, K. W. Chiu, and T. Yoshida, J. Org. Chem., 1975, 40, 1676.

[6]L. S. Hegedus, P. M. Kendall, S. M. Lo, and J. R. Sheats, J. Am. Chem. Soc., 1975, 97, 5448.

[7]P. F. Hudrlik, J. Organomet. Chem. Libr., 1976, 1, 127–159.

[8]R. C. Larock, J. Organomet. Chem. Libr., 1976, 1, 257–303.

[9]G. Cahiez, D. Bernard, and J. F. Normant, Synthesis, 1977, 130.

[10]D. B. Carr and J. Schwartz, J. Am. Chem. Soc., 1979, 101, 3521.

[11]A. N. Kashin, N. A. Bumagin, I. O. Kalinovski, I. P. Beletskaya, and O. A. Reutov, Zh. Org. Khim., 1980, 16, 1569.

[12]H.-U. Blaser and A. Spencer, J. Organomet. Chem., 1982, 233, 267.

[13]T. Sato, K. Naruse, M. Enokiya, and T. Fujisawa, Chem. Lett., 1981, 1135.

[14]T. Sato, T. Itoh, and T. Fujisawa, Chem. Lett., 1982, 1559.

[15]E. Negishi, V. Bagheri, S. Chatterjee, F.-T. Luo, J. A. Miller, and A. T. Stoll, Tetrahedron Lett., 1983, 24, 5181.

[16]Y. Tamaru, H. Ochiai, T. Nakamura, and Z. Yoshida, Tetrahedron Lett., 1986, 27, 955.

[17]E. Negishi, N. Okukado, A. O. King, D. E. Van Horn, and B. I. Spiegel, J. Am. Chem. Soc., 1978, 100, 2254.

[18]E. Negishi, A. O. King, and N. Okukado, J. Org. Chem., 1977, 42, 1821.

[19]R. F. Heck, Org. React., 1982, 27, 345–390.

[20]R. A. Grey, J. Org. Chem., 1984, 49, 2288.

[21]Y. Kondo, M. Uchiyama, and T. Sakamoto, J. Synth. Org. Chem. Jpn., 1997, 55, 547.

[22]E. Negishi, T. Takahashi, and K. Akiyoshi, J. Chem. Soc. Chem. Commun., 1986, 1338.

[23]R. F. W. Jackson, N. Wishart, A. Wood, K. James, and M. J. Wythes, J. Org. Chem., 1992, 57, 3397.

[24]T. Houkawa, T. Ueda, S. Sakami, M. Asaoka, and H. Takei, Tetrahedron Lett., 1996, 37, 1045.

[25]Y. Tamaru, H. Ochiai, F. Sanda, and Z. Yoshida, Tetrahedron Lett., 1985, 26, 5529.

[26]M. M. Faul and L. L. Winneroski, Tetrahedron Lett., 1997, 38, 4749.

III.2.12.1 CROSS-COUPLING WITH ACYL HALIDES

647

[27]R. F. Heck, J. Am. Chem. Soc., 1968, 90, 5518.

[28]M. Kosugi, Y. Shimizu, and T. Migita, Chem. Lett., 1977, 1423.

[29]D. Milstein and J. K. Stille, J. Am. Chem. Soc., 1978, 100, 3636.

[30]P. Four and F. Guibe, J. Org. Chem., 1981, 46, 4439.

[31]L. S. Liebeskind, M. S. Yu, and R. W. Fengl, J. Org. Chem., 1993, 58, 3543.

[32]M. W. Logue and K. Teng, J. Org. Chem., 1982, 47, 2549.

[33]J. W. Labadie D. Tueting, and J. K. Stille, J. Org. Chem., 1983, 48, 4634.

[34]J. Godschalx and J. K. Stille, Tetrahedron Lett., 1980, 21, 2599.

[35]J. W. Labadie and J. K. Stille, J. Am. Chem. Soc., 1983, 105, 6129.

[36]J.-L. Parrain, A. Duchêne, and J.-P. Quintard, Tetrahedron Lett., 1990, 31, 1857.

[37]Y. Ito, M. Inouye, and M. Murakami, Tetrahedron Lett., 1988, 29, 5379.

[38]V. Farina and B. Krishnan, J. Am. Chem. Soc., 1991, 113, 9585.

[39]J. Ye, R. K. Bhatt, and J. R. Falck, Tetrahedron Lett., 1993, 34, 8007.

[40]J. Ye, R. K. Bhatt, and J. R. Falck, J. Am. Chem. Soc., 1994, 116, 1.

[41]M. Pérez, A. M. Castaño, and A. M. Echavarren, J. Org. Chem., 1992, 57, 5047.

[42]K. Takagi, T. Okamoto, Y. Sakakibara, A. Ohno, S. Oka, and N. Hayama, Chem. Lett., 1975, 951.

[43]N. A. Bumagin, I. G. Bumagina, A. N. Kashin, and I. P. Beletskaya, Zh. Org, Khim., 1982, 18, 1131.

[44]I. P. Beletskaya, J. Organomet. Chem., 1983, 250, 551.

[45]L. S. Hegedus, M. R. Sestrick, E. T. Michaelson, and P. J. Harrington, J. Org. Chem., 1989, 54, 4141.

[46]E. Negishi, A. Abramovitch, and R. E. Merrill, J. Chem. Soc. Chem. Commun., 1975, 138.

[47]C. S. Cho, K. Itotani, and S. Uemura, J. Organomet. Chem., 1993, 443, 253.

[48]K. Wakamatsu, Y. Okuda, K. Oshima, and H. Nozaki, Bull. Chem. Soc. Jpn., 1985, 58, 2425.

[49]Y. Hanzawa, N. Tabuchi, and T. Taguchi, Tetrahedron Lett., 1998, 39, 6249.

[50]N. Jabri, A. Alexakis, and J. F. Normant, Tetrahedron Lett., 1983, 24, 5081.

[51]Y. Tohda, K. Sonogashira, and N. Hagihara, Synthesis, 1977, 777.

[52]Y. Tanaka, H. Yamashita, and M. Tanaka, Organometallics, 1996, 15, 1524.

[53]J. Yamada and Y. Yamamoto, J. Chem. Soc. Chem. Commun., 1987, 1302.

[54]D. H. R. Barton, N. Ozbalik, and M. Ramesh, Tetrahedron, 1988, 44, 5661.

[55]S. Aoki, T. Fujimura, E. Nakamura, and I. Kuwajima, Tetrahedron Lett., 1989, 30, 6541.