Alkynes as activators in the nickel-catalysed addition of organoboronates to aldehydes

Chemical Communications

Volumn , Issue 11, 2005, Pages 1459-1461

  Takahashi, Go ^a   Shirakawa, Eiji ^b   Tsuchimoto, Teruhisa ^a   Kawakami, Yusuke ^a  

^a JAPAN ADVANCED INSTITUTE OF SCIENCE AND TECHNOLOGY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALKYNE; BORONIC ACID DERIVATIVE; NICKEL; ORGANOBORON DERIVATIVE; ORGANOBORONATE DERIVATIVE; UNCLASSIFIED DRUG; WATER;

ADDITION REACTION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHEMICAL REACTION; CONCENTRATION RESPONSE; REACTION ANALYSIS; REPRODUCIBILITY; TECHNIQUE;

EID: 16444382687     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b417353h     Document Type: Article

References (41)

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6. For the palladium- or nickel-catalysed carbostannylation of alkynes, see: E. Shirakawa, H. Yoshida, T. Kurahashi, Y. Nakao and T. Hiyama, J. Am. Chem. Soc., 1998, 120, 2975-2976; E. Shirakawa, H. Yoshida, Y. Nakao and T. Hiyama, J. Am. Chem. Soc., 1999, 121, 4290-4291; E. Shirakawa, K. Yamasaki, H. Yoshida and T. Hiyama, J. Am. Chem. Soc., 1999, 121, 10221-10222; E. Shirakawa, H. Yoshida, Y. Nakao and T. Hiyama, Org. Lett., 2000, 2, 2209-2211; H. Yoshida, E. Shirakawa, T. Kurahashi, Y. Nakao and T. Hiyama, Organometallics, 2000, 19, 5671-5678; E. Shirakawa, Y. Yamamoto, Y. Nakao, T. Tsuchimoto and T. Hiyama, Chem. Commun., 2001, 1926-1927; H. Yoshida, E. Shirakawa, Y. Nakao, Y. Honda and T. Hiyama, Bull. Chem. Soc. Jpn., 2001, 74, 637-647.
7. For the palladium- or nickel-catalysed carbostannylation of alkynes, see: E. Shirakawa, H. Yoshida, T. Kurahashi, Y. Nakao and T. Hiyama, J. Am. Chem. Soc., 1998, 120, 2975-2976; E. Shirakawa, H. Yoshida, Y. Nakao and T. Hiyama, J. Am. Chem. Soc., 1999, 121, 4290-4291; E. Shirakawa, K. Yamasaki, H. Yoshida and T. Hiyama, J. Am. Chem. Soc., 1999, 121, 10221-10222; E. Shirakawa, H. Yoshida, Y. Nakao and T. Hiyama, Org. Lett., 2000, 2, 2209-2211; H. Yoshida, E. Shirakawa, T. Kurahashi, Y. Nakao and T. Hiyama, Organometallics, 2000, 19, 5671-5678; E. Shirakawa, Y. Yamamoto, Y. Nakao, T. Tsuchimoto and T. Hiyama, Chem. Commun., 2001, 1926-1927; H. Yoshida, E. Shirakawa, Y. Nakao, Y. Honda and T. Hiyama, Bull. Chem. Soc. Jpn., 2001, 74, 637-647.
8. For the palladium- or nickel-catalysed carbostannylation of alkynes, see: E. Shirakawa, H. Yoshida, T. Kurahashi, Y. Nakao and T. Hiyama, J. Am. Chem. Soc., 1998, 120, 2975-2976; E. Shirakawa, H. Yoshida, Y. Nakao and T. Hiyama, J. Am. Chem. Soc., 1999, 121, 4290-4291; E. Shirakawa, K. Yamasaki, H. Yoshida and T. Hiyama, J. Am. Chem. Soc., 1999, 121, 10221-10222; E. Shirakawa, H. Yoshida, Y. Nakao and T. Hiyama, Org. Lett., 2000, 2, 2209-2211; H. Yoshida, E. Shirakawa, T. Kurahashi, Y. Nakao and T. Hiyama, Organometallics, 2000, 19, 5671-5678; E. Shirakawa, Y. Yamamoto, Y. Nakao, T. Tsuchimoto and T. Hiyama, Chem. Commun., 2001, 1926-1927; H. Yoshida, E. Shirakawa, Y. Nakao, Y. Honda and T. Hiyama, Bull. Chem. Soc. Jpn., 2001, 74, 637-647.
9. For the palladium- or nickel-catalysed carbostannylation of alkynes, see: E. Shirakawa, H. Yoshida, T. Kurahashi, Y. Nakao and T. Hiyama, J. Am. Chem. Soc., 1998, 120, 2975-2976; E. Shirakawa, H. Yoshida, Y. Nakao and T. Hiyama, J. Am. Chem. Soc., 1999, 121, 4290-4291; E. Shirakawa, K. Yamasaki, H. Yoshida and T. Hiyama, J. Am. Chem. Soc., 1999, 121, 10221-10222; E. Shirakawa, H. Yoshida, Y. Nakao and T. Hiyama, Org. Lett., 2000, 2, 2209-2211; H. Yoshida, E. Shirakawa, T. Kurahashi, Y. Nakao and T. Hiyama, Organometallics, 2000, 19, 5671-5678; E. Shirakawa, Y. Yamamoto, Y. Nakao, T. Tsuchimoto and T. Hiyama, Chem. Commun., 2001, 1926-1927; H. Yoshida, E. Shirakawa, Y. Nakao, Y. Honda and T. Hiyama, Bull. Chem. Soc. Jpn., 2001, 74, 637-647.
10. For the palladium- or nickel-catalysed carbostannylation of alkynes, see: E. Shirakawa, H. Yoshida, T. Kurahashi, Y. Nakao and T. Hiyama, J. Am. Chem. Soc., 1998, 120, 2975-2976; E. Shirakawa, H. Yoshida, Y. Nakao and T. Hiyama, J. Am. Chem. Soc., 1999, 121, 4290-4291; E. Shirakawa, K. Yamasaki, H. Yoshida and T. Hiyama, J. Am. Chem. Soc., 1999, 121, 10221-10222; E. Shirakawa, H. Yoshida, Y. Nakao and T. Hiyama, Org. Lett., 2000, 2, 2209-2211; H. Yoshida, E. Shirakawa, T. Kurahashi, Y. Nakao and T. Hiyama, Organometallics, 2000, 19, 5671-5678; E. Shirakawa, Y. Yamamoto, Y. Nakao, T. Tsuchimoto and T. Hiyama, Chem. Commun., 2001, 1926-1927; H. Yoshida, E. Shirakawa, Y. Nakao, Y. Honda and T. Hiyama, Bull. Chem. Soc. Jpn., 2001, 74, 637-647.
11. For the palladium- or nickel-catalysed carbostannylation of alkynes, see: E. Shirakawa, H. Yoshida, T. Kurahashi, Y. Nakao and T. Hiyama, J. Am. Chem. Soc., 1998, 120, 2975-2976; E. Shirakawa, H. Yoshida, Y. Nakao and T. Hiyama, J. Am. Chem. Soc., 1999, 121, 4290-4291; E. Shirakawa, K. Yamasaki, H. Yoshida and T. Hiyama, J. Am. Chem. Soc., 1999, 121, 10221-10222; E. Shirakawa, H. Yoshida, Y. Nakao and T. Hiyama, Org. Lett., 2000, 2, 2209-2211; H. Yoshida, E. Shirakawa, T. Kurahashi, Y. Nakao and T. Hiyama, Organometallics, 2000, 19, 5671-5678; E. Shirakawa, Y. Yamamoto, Y. Nakao, T. Tsuchimoto and T. Hiyama, Chem. Commun., 2001, 1926-1927; H. Yoshida, E. Shirakawa, Y. Nakao, Y. Honda and T. Hiyama, Bull. Chem. Soc. Jpn., 2001, 74, 637-647.
12. For the nickel-catalysed addition of arylboron compounds to alkynes, see: E. Shirakawa, G. Takahashi, T. Tsuchimoto and Y. Kawakami, Chem. Commun., 2001, 2688-2689.
13. E. Oblinger and J. Montgomery, J. Am. Chem. Soc, 1997, 119, 9065-9066; X.-Q. Tang and J. Montgomery, J. Am. Chem. Soc., 1999, 121, 6098-6099; X.-Q. Tang and J. Montgomery, J. Am. Chem. Soc., 2000, 122, 6950-6954; W.-S. Huang, J. Chan and T. F. Jamison, Org. Lett., 2000, 2, 4221-4223; E. A. Colby and T. F. Jamison, J. Org. Chem., 2003, 68, 156-166; K. M. Miller, W.-S. Huang and T. F. Jamison, J. Am. Chem. Soc., 2003, 125, 3442-3443; K. M. Miller, T. Luanphaisarnnont, C. Molinaro and T. F. Jamison, J. Am. Chem. Soc., 2004, 126, 4130-4131.
14. E. Oblinger and J. Montgomery, J. Am. Chem. Soc, 1997, 119, 9065-9066; X.-Q. Tang and J. Montgomery, J. Am. Chem. Soc., 1999, 121, 6098-6099; X.-Q. Tang and J. Montgomery, J. Am. Chem. Soc., 2000, 122, 6950-6954; W.-S. Huang, J. Chan and T. F. Jamison, Org. Lett., 2000, 2, 4221-4223; E. A. Colby and T. F. Jamison, J. Org. Chem., 2003, 68, 156-166; K. M. Miller, W.-S. Huang and T. F. Jamison, J. Am. Chem. Soc., 2003, 125, 3442-3443; K. M. Miller, T. Luanphaisarnnont, C. Molinaro and T. F. Jamison, J. Am. Chem. Soc., 2004, 126, 4130-4131.
15. E. Oblinger and J. Montgomery, J. Am. Chem. Soc, 1997, 119, 9065-9066; X.-Q. Tang and J. Montgomery, J. Am. Chem. Soc., 1999, 121, 6098-6099; X.-Q. Tang and J. Montgomery, J. Am. Chem. Soc., 2000, 122, 6950-6954; W.-S. Huang, J. Chan and T. F. Jamison, Org. Lett., 2000, 2, 4221-4223; E. A. Colby and T. F. Jamison, J. Org. Chem., 2003, 68, 156-166; K. M. Miller, W.-S. Huang and T. F. Jamison, J. Am. Chem. Soc., 2003, 125, 3442-3443; K. M. Miller, T. Luanphaisarnnont, C. Molinaro and T. F. Jamison, J. Am. Chem. Soc., 2004, 126, 4130-4131.
16. E. Oblinger and J. Montgomery, J. Am. Chem. Soc, 1997, 119, 9065-9066; X.-Q. Tang and J. Montgomery, J. Am. Chem. Soc., 1999, 121, 6098-6099; X.-Q. Tang and J. Montgomery, J. Am. Chem. Soc., 2000, 122, 6950-6954; W.-S. Huang, J. Chan and T. F. Jamison, Org. Lett., 2000, 2, 4221-4223; E. A. Colby and T. F. Jamison, J. Org. Chem., 2003, 68, 156-166; K. M. Miller, W.-S. Huang and T. F. Jamison, J. Am. Chem. Soc., 2003, 125, 3442-3443; K. M. Miller, T. Luanphaisarnnont, C. Molinaro and T. F. Jamison, J. Am. Chem. Soc., 2004, 126, 4130-4131.
17. E. Oblinger and J. Montgomery, J. Am. Chem. Soc, 1997, 119, 9065-9066; X.-Q. Tang and J. Montgomery, J. Am. Chem. Soc., 1999, 121, 6098-6099; X.-Q. Tang and J. Montgomery, J. Am. Chem. Soc., 2000, 122, 6950-6954; W.-S. Huang, J. Chan and T. F. Jamison, Org. Lett., 2000, 2, 4221-4223; E. A. Colby and T. F. Jamison, J. Org. Chem., 2003, 68, 156-166; K. M. Miller, W.-S. Huang and T. F. Jamison, J. Am. Chem. Soc., 2003, 125, 3442-3443; K. M. Miller, T. Luanphaisarnnont, C. Molinaro and T. F. Jamison, J. Am. Chem. Soc., 2004, 126, 4130-4131.
18. E. Oblinger and J. Montgomery, J. Am. Chem. Soc, 1997, 119, 9065-9066; X.-Q. Tang and J. Montgomery, J. Am. Chem. Soc., 1999, 121, 6098-6099; X.-Q. Tang and J. Montgomery, J. Am. Chem. Soc., 2000, 122, 6950-6954; W.-S. Huang, J. Chan and T. F. Jamison, Org. Lett., 2000, 2, 4221-4223; E. A. Colby and T. F. Jamison, J. Org. Chem., 2003, 68, 156-166; K. M. Miller, W.-S. Huang and T. F. Jamison, J. Am. Chem. Soc., 2003, 125, 3442-3443; K. M. Miller, T. Luanphaisarnnont, C. Molinaro and T. F. Jamison, J. Am. Chem. Soc., 2004, 126, 4130-4131.
19. E. Oblinger and J. Montgomery, J. Am. Chem. Soc, 1997, 119, 9065-9066; X.-Q. Tang and J. Montgomery, J. Am. Chem. Soc., 1999, 121, 6098-6099; X.-Q. Tang and J. Montgomery, J. Am. Chem. Soc., 2000, 122, 6950-6954; W.-S. Huang, J. Chan and T. F. Jamison, Org. Lett., 2000, 2, 4221-4223; E. A. Colby and T. F. Jamison, J. Org. Chem., 2003, 68, 156-166; K. M. Miller, W.-S. Huang and T. F. Jamison, J. Am. Chem. Soc., 2003, 125, 3442-3443; K. M. Miller, T. Luanphaisarnnont, C. Molinaro and T. F. Jamison, J. Am. Chem. Soc., 2004, 126, 4130-4131.
20. The three-component coupling between phenylboronic acid, 1-phenylpropyne and an imine derived from benzaldehyde has been reported. S. J. Patel and T. F. Jamison, Angew. Chem. Int. Ed., 2003, 42, 1364-1367.
21. To the best of our knowledge, there has been no report on the transition metal-catalysed addition of organoboron compounds to aldehydes except for the rhodium-catalysed reaction. M. Sakai, M. Ueda and N. Miyaura, Angew. Chem. Int. Ed., 1998, 37, 3279-3281; M. Ueda and N. Miyaura, J. Org. Chem., 2000, 65, 4450-4452; A. Fürstner and H. Krause, Adv. Synth. Catal., 2001, 343, 343-350; C. Moreau, C. Hague, A. S. Weller and C. G. Frost, Tetrahedron Lett., 2001, 42, 6957-6960. See also ref. 9.
22. To the best of our knowledge, there has been no report on the transition metal-catalysed addition of organoboron compounds to aldehydes except for the rhodium-catalysed reaction. M. Sakai, M. Ueda and N. Miyaura, Angew. Chem. Int. Ed., 1998, 37, 3279-3281; M. Ueda and N. Miyaura, J. Org. Chem., 2000, 65, 4450-4452; A. Fürstner and H. Krause, Adv. Synth. Catal., 2001, 343, 343-350; C. Moreau, C. Hague, A. S. Weller and C. G. Frost, Tetrahedron Lett., 2001, 42, 6957-6960. See also ref. 9.
23. To the best of our knowledge, there has been no report on the transition metal-catalysed addition of organoboron compounds to aldehydes except for the rhodium-catalysed reaction. M. Sakai, M. Ueda and N. Miyaura, Angew. Chem. Int. Ed., 1998, 37, 3279-3281; M. Ueda and N. Miyaura, J. Org. Chem., 2000, 65, 4450-4452; A. Fürstner and H. Krause, Adv. Synth. Catal., 2001, 343, 343-350; C. Moreau, C. Hague, A. S. Weller and C. G. Frost, Tetrahedron Lett., 2001, 42, 6957-6960. See also ref. 9.
24. To the best of our knowledge, there has been no report on the transition metal-catalysed addition of organoboron compounds to aldehydes except for the rhodium-catalysed reaction. M. Sakai, M. Ueda and N. Miyaura, Angew. Chem. Int. Ed., 1998, 37, 3279-3281; M. Ueda and N. Miyaura, J. Org. Chem., 2000, 65, 4450-4452; A. Fürstner and H. Krause, Adv. Synth. Catal., 2001, 343, 343-350; C. Moreau, C. Hague, A. S. Weller and C. G. Frost, Tetrahedron Lett., 2001, 42, 6957-6960. See also ref. 9.
25. Asymmetric addition of arylboronates to aromatic aldehydes mediated by an excess amount of diexhylzinc in the presence of a chiral oxazolylalcohol has been reported. C. Bolm and J. Rudolph, J. Am. Chem. Soc., 2002, 124, 14850-14851.
26. Addition products of triphenylborane to aldehydes were produced as | by-products (yield ≤ 22%) in the nickel-catalysed three-component coupling between triphenylborane, isoprene and aldehydes. K. Shibata, M. Kimura, K. Kojima, S. Tanaka and Y. Tamaru, J. Organomet. Chem., 2001, 624, 348-353.
27. 2O has played a crucial role in the nickel-catalysed hydroarylation of alkynes or 1,3-dienes using arylboronates. For alkynes, see ref. 4. For 1,3-dienes, see: E. Shirakawa, G. Takahashi, T. Tsuchimoto and Y. Kawakami, Chem. Commun., 2002, 2210-2211.
28. Although the role of water is not clear at present, it may act as a Lewis base that coordinates to the boron atom and promotes the attack of the aryl groups on the aldehyde carbons.
29. 2O in 1,4-dioxane at 80 °C for 6 h.
30. p-Tolylboronic acid did not add to 2a at all under the conditions identical to entry 6 in Table 1.
31. 1H NMR, respectively.
32. For reviews of transition metal-catalysed reactions in aqueous media, see: C.-J. Li and T.-H. Chan, Organic Reactions in Aqueous Media, John Wiley, New York, 1997, pp. 115-160; B. Cornils and W. A. Herrmann, Aqueous-Phase Organometallic Chemistry, Wiley-VCH, Weinheim, 1998; D. Sinou, in Modern Solvents in Organic Synthesis, ed. P. Knochel, Springer, Berlin, 1999, pp. 41-59.
33. For reviews of transition metal-catalysed reactions in aqueous media, see: C.-J. Li and T.-H. Chan, Organic Reactions in Aqueous Media, John Wiley, New York, 1997, pp. 115-160; B. Cornils and W. A. Herrmann, Aqueous-Phase Organometallic Chemistry, Wiley-VCH, Weinheim, 1998; D. Sinou, in Modern Solvents in Organic Synthesis, ed. P. Knochel, Springer, Berlin, 1999, pp. 41-59.
34. For reviews of transition metal-catalysed reactions in aqueous media, see: C.-J. Li and T.-H. Chan, Organic Reactions in Aqueous Media, John Wiley, New York, 1997, pp. 115-160; B. Cornils and W. A. Herrmann, Aqueous-Phase Organometallic Chemistry, Wiley-VCH, Weinheim, 1998; D. Sinou, in Modern Solvents in Organic Synthesis, ed. P. Knochel, Springer, Berlin, 1999, pp. 41-59.
35. 1H NMR).
36. The triethylborane-promoted, nickel-catalysed homoallylation of glutaraldehyde in an aqueous media lias been reported. M. Kimura, A. Ezoe, S. Tanaka and Y. Tamaru, Angew. Chem. Int. Ed., 2001, 40, 3600-3602.
37. Although we have not determined the stereochemistry of each compound, the observation that the isomers were transformed to a single lactone after oxidation should show that they are diastereomers.
38. E. J. Corey and J. W. Suggs, Tetrahedron Lett., 1975, 31, 2547-2650.
39. Grigg and co-workers proposed the potentiality of alkynes as activators in the rhodium-catalysed cyclization of unconjugated enynes, where the enynes act both as substrates and co-catalysts adding oxidatively to a rhodium(I) catalyst at their terminal acetylenic C-H bond. R. Grigg, P. Stevenson and T. Worakun, Tetrahedron, 1988, 44, 4967-4972.
40. Furthermore, in the rhodium-bisphosphine-catalysed successive cleavage of carbon-carbon and carbon-oxygen bonds of 2-(alkoxymethyl)-cyclobutanones, diphenylacetylene was used as an effective co-ligand, which is thought to coordinate to a rhodium-bisphosphine complex inhibiting unfavorable coordination of the olefinic moiety of the substrates. M. Murakami, T. Itahashi, A. Amii, K. Takahashi and Y. Ito, J. Am. Chem. Soc., 1998, 120, 9949-9950.
41. Considering the significant number of examples of an alkyne and an aldehyde undergoing oxidative cyclization with a nickel(0) complex to give a 2-oxanickellacyclopent-4-ene, there might be some possibility that the reaction proceeds through the nickellacycles, which react with organoboronates with cleavage of the C(3)-C(4) bond to afford addition product 3, the nickel(0) complex and 4-octyne. See ref. 5. Oxidative cyclization of enals to nickel(o) complexes to afford 2-oxanickellacyclopentanes also has recently been reported. S. Ososhi, M. Oka and H. Kurosawa, J. Am. Chem. Soc., 2004, 126, 11802-11803.