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Reactions of Alkynylboron Compounds

Chapter
Part of the Topics in Organometallic Chemistry book series (TOPORGAN, volume 49)

Abstract

This chapter overviews reactions of alkynylboron compounds, in which the carbon–carbon triple bond is transformed into a different form, with the boryl group remaining in the product. Most of the reactions produce multiply substituted alkenyl- and aryl-boron compounds.

Keywords

Alkyne Boron Catalysis Directing group Organic synthesis Regioselectivity Transition metal 

References

  1. 1.
    Miyaura N, Suzuki A (1995) Chem Rev 95:2457Google Scholar
  2. 2.
    Negishi E (1976) J Organomet Chem 108:281Google Scholar
  3. 3.
    Cragg GML, Koch KR (1977) Chem Soc Rev 6:393Google Scholar
  4. 4.
    Suzuki A (1982) Acc Chem Res 15:78Google Scholar
  5. 5.
    Hilt G, Bolze P (2005) Synthesis 2091Google Scholar
  6. 6.
    Jiao J, Nishihara Y (2012) J Organomet Chem 721–722:3Google Scholar
  7. 7.
    Brown HC, Bhat NG, Srebnik M (1988) Tetrahedron Lett 29:2631Google Scholar
  8. 8.
    Lee C-I, Zhou J, Ozerov OV (2013) J Am Chem Soc 135:3560Google Scholar
  9. 9.
    Deloux L, Skrzypczak-Jankun E, Cheesman BV, Srebnik M, Savat M (1994) J Am Chem Soc 116:10302Google Scholar
  10. 10.
    Gu Y, Pritzkow H, Siebert W (2001) Eur J Inorg Chem 373Google Scholar
  11. 11.
    Li H, Carroll PJ, Walsh PJ (2008) J Am Chem Soc 130:3521Google Scholar
  12. 12.
    Weber L, Eickhoff D, Halama J, Werner S, Kahlert J, Stammler H-G, Neumann B (2013) Eur J Inorg Chem 2608Google Scholar
  13. 13.
    Soderquist JA, Rane AM, Matos K, Ramos J (1995) Tetrahedron Lett 36:6847Google Scholar
  14. 14.
    Struble JR, Lee SJ, Burke MD (2010) Tetrahedron 66:4710Google Scholar
  15. 15.
    Ohmura T, Suginome M (2009) Bull Chem Soc Jpn 82:29Google Scholar
  16. 16.
    Jiao J, Nakajima K, Nishihara Y (2013) Org Lett 15:3294Google Scholar
  17. 17.
    Matteson DS, Waldbillig JO (1963) J Org Chem 28:366Google Scholar
  18. 18.
    Woods WG, Strong PL (1967) J Organomet Chem 7:371Google Scholar
  19. 19.
    Singleton DA, Leunt S-W (1992) J Org Chem 57:4796Google Scholar
  20. 20.
    Leung S-W, Singleton DA (1997) J Org Chem 62:1955Google Scholar
  21. 21.
    Silva MA, Pellegrinet SC, Goodman JM (2002) J Org Chem 67:8203Google Scholar
  22. 22.
    Silva MA, Pellegrinet SC, Goodman JM (2003) J Org Chem 68:4059Google Scholar
  23. 23.
    Seitz G, Haenel F (1994) Arch Pharm 327:673Google Scholar
  24. 24.
    Helm MD, Moore JE, Plant A, Harrity JPA (2005) Angew Chem Int Ed 44:3889Google Scholar
  25. 25.
    Gomez-Bengoa E, Helm MD, Plant A, Harrity JPA (2007) J Am Chem Soc 129:2691Google Scholar
  26. 26.
    Moore JE, York M, Harrity JPA (2005) Synlett 860Google Scholar
  27. 27.
    Delaney PM, Moore JE, Harrity JPA (2006) Chem Commun 3323Google Scholar
  28. 28.
    Delaney PM, Browne DL, Adams H, Plant A, Harrity JPA (2008) Tetrahedron 64:866Google Scholar
  29. 29.
    Kirkham JD, Leach AG, Row EC, Harrity JPA (2012) Synthesis 44:1964Google Scholar
  30. 30.
    Delaney PM, Huang J, Macdonald SJF, Harrity JPA (2007) Org Lett 10:781Google Scholar
  31. 31.
    Kirkham JD, Butlin RJ, Harrity JPA (2012) Angew Chem Int Ed 51:6402Google Scholar
  32. 32.
    Crepin DFP, Harrity JPA, Jiang J, Meijer AJHM, Nassoy A-CMA, Raubo P (2014) J Am Chem Soc 136:8642Google Scholar
  33. 33.
    Vivat JF, Adams H, Harrity JPA (2010) Org Lett 12:160Google Scholar
  34. 34.
    Matteson DS (1962) J Org Chem 27:4293Google Scholar
  35. 35.
    Davies MW, Wybrow RAJ, Johnson CN, Harrity JPA (2001) Chem Commun 1558Google Scholar
  36. 36.
    Huang J, Macdonald SJF, Harrity JPA (2009) Chem Commun 436Google Scholar
  37. 37.
    Browne DL, Helm MD, Plant A, Harrity JPA (2007) Angew Chem Int Ed 46:8656Google Scholar
  38. 38.
    Browne DL, Vivat JF, Plant A, Gomez-Bengoa E, Harrity JPA (2009) J Am Chem Soc 131:7762Google Scholar
  39. 39.
    Kirkham JD, Edeson SJ, Stokes S, Harrity JPA (2012) Org Lett 14:5354Google Scholar
  40. 40.
    Maderna A, Pritzkow H, Siebert W (1996) Angew Chem Int Ed 35:1501Google Scholar
  41. 41.
    Ester C, Maderna A, Pritzkow H, Siebert W (2000) Eur J Inorg Chem 1177Google Scholar
  42. 42.
    Goswami A, Pritzkow H, Rominger F, Siebert W (2004) Eur J Inorg Chem 4223Google Scholar
  43. 43.
    Gandon V, Leca D, Aechtner T, Vollhardt KPC, Malacria M, Aubert C (2004) Org Lett 6:3405Google Scholar
  44. 44.
    Gandon V, Leboeuf D, Amslinger S, Vollhardt KPC, Malacria M, Aubert C (2005) Angew Chem Int Ed 44:7114Google Scholar
  45. 45.
    Geny A, Leboeuf D, Rouquie G, Vollhardt KPC, Malacria M, Gandon V, Aubert C (2007) Chem Eur J 13:5408Google Scholar
  46. 46.
    Hilt G, Smolko KI (2003) Angew Chem Int Ed 42:2795Google Scholar
  47. 47.
    Auvinet A-L, Harrity JPA, Hilt G (2010) J Org Chem 75:3893Google Scholar
  48. 48.
    Yamamoto Y, Ishii J, Nishiyama H, Itoh K (2004) J Am Chem Soc 126:3712Google Scholar
  49. 49.
    Yamamoto Y, Ishii J, Nishiyama H, Itoh K (2005) Tetrahedron 61:11501Google Scholar
  50. 50.
    Yamamoto Y, Hattori K, Ishii J, Nishiyama H (2006) Tetrahedron 62:4294Google Scholar
  51. 51.
    Miura T, Yamauchi M, Murakami M (2008) Org Lett 10:3085Google Scholar
  52. 52.
    Huffman MA, Liebeskind LS (1991) J Am Chem Soc 113:2771Google Scholar
  53. 53.
    Auvinet A-L, Harrity JPA (2011) Angew Chem Int Ed 50:2769Google Scholar
  54. 54.
    Negishi E, Takahashi T (1998) Synthesis 1Google Scholar
  55. 55.
    Quintar AAA, Srebnik M (2004) Org Lett 6:4243Google Scholar
  56. 56.
    Nishihara Y, Miyasaka M, Okamoto M, Takahashi H, Inoue E, Tanemura K, Takagi K (2007) J Am Chem Soc 129:12634Google Scholar
  57. 57.
    Nishihara Y, Okada Y, Jiao J, Suetsugu M, Lan M-T, Kinoshita M, Iwasaki M, Takagi K (2011) Angew Chem Int Ed 50:8660Google Scholar
  58. 58.
    Desurmont G, Klein R, Uhlenbrock S, Laloe E, Deloux L, Giolando DM, Kim YW, Pereira S, Srebnik M (1996) Organometallics 15:3323Google Scholar
  59. 59.
    Metzler N, Nöth H, Thomann M (1993) Organometallics 12:2423Google Scholar
  60. 60.
    Altenburger K, Arndt P, Spannenberg A, Baumann W, Rosenthal U (2013) Eur J Inorg Chem 3200Google Scholar
  61. 61.
    Davies MW, Harrity JPA, Johnson CN (1999) Chem Commun 2107Google Scholar
  62. 62.
    Davies MW, Johnson CN, Harrity JPA (2001) J Org Chem 3525Google Scholar
  63. 63.
    Dötz KH, Tomuschat P (1999) Chem Soc Rev 28:187Google Scholar
  64. 64.
    Barluenga J, Barrio P, Riesgo L, Lopez LA, Tomas M (2007) J Am Chem Soc 129:14422Google Scholar
  65. 65.
    Poulsen CS, Madsen R (2003) Synthesis 1Google Scholar
  66. 66.
    Giessert AJ, Diver ST (2004) Chem Rev 104:1317Google Scholar
  67. 67.
    Micalizio GC, Schreiber SL (2002) Angew Chem Int Ed 41:3272Google Scholar
  68. 68.
    Kim M, Lee D (2005) Org Lett 7:1865Google Scholar
  69. 69.
    Renaud J, Graf C-D, Oberer L (2000) Angew Chem Int Ed 39:3101Google Scholar
  70. 70.
    Ko HM, Lee CW, Kwon HK, Chung HS, Choi SY, Chung YK, Lee E (2009) Angew Chem Int Ed 48:2364Google Scholar
  71. 71.
    Belmont P, Parker E (2009) Eur J Org Chem 6075Google Scholar
  72. 72.
    Lee JCH, Hall DG (2011) Tetrahedron Lett 52:321Google Scholar
  73. 73.
    Trost BM, Toste FD, Pinkerton AB (2001) Chem Rev 101:2067Google Scholar
  74. 74.
    Hansen EC, Lee D (2005) J Am Chem Soc 127:3252Google Scholar
  75. 75.
    Trost BM, Machacek M, Schnaderbeck MJ (2000) Org Lett 2:1761Google Scholar
  76. 76.
    Suginome M, Shirakura M, Yamamoto A (2006) J Am Chem Soc 128:14438Google Scholar
  77. 77.
    Binger P, Köster R (1965) Tetrahedron Lett 6:1901Google Scholar
  78. 78.
    Binger P, Benedikt G, Rotermund GW, Köster R (1968) Liebigs Ann Chem 717:21Google Scholar
  79. 79.
    Ishida N, Shimamoto Y, Murakami M (2009) Org Lett 11:5434Google Scholar
  80. 80.
    Dureen MA, Stephan DW (2009) J Am Chem Soc 131:8396Google Scholar
  81. 81.
    Miyaura N, Yoshinari T, Itoh M, Suzuki A (1974) Tetrahedron Lett 15:2961Google Scholar
  82. 82.
    Brown HC, Levy AB, Midland MM (1975) J Am Chem Soc 97:501Google Scholar
  83. 83.
    Pelter A, Harrison CR, Subrahmanyam C, Kirkpatrick D (1976) J Chem Soc Perkin Trans 1:2435Google Scholar
  84. 84.
    Pelter A, Harrison CR, Kirkpatrick (1973) J Chem Soc Chem Commun 544Google Scholar
  85. 85.
    Pelter A, Subrahmanyam C, Laub RJ, Gould KJ, Harrison CR (1975) Tetrahedron Lett 1633Google Scholar
  86. 86.
    Pelter A, Bentley TW, Harrison CR, Subrahmanyam C, Laub RJ (1976) J Chem Soc Perkin Trans 1:2419Google Scholar
  87. 87.
    Pelter A, Gould KJ, Harrison CR (1976) J Chem Soc Perkin Trans 1:2428Google Scholar
  88. 88.
    Deng M, Tang Y, Xu W (1984) Tetrahedron 25:1797Google Scholar
  89. 89.
    Binger P, Köster R (1974) J Organomet Chem 73:205Google Scholar
  90. 90.
    Gerard J, Hevesi L (2001) Tetrahedron 57:9109Google Scholar
  91. 91.
    Binger P, Köster R (1973) Synthesis 309Google Scholar
  92. 92.
    Hooz J, Mortimer R (1976) Tetrahedron Lett 17:805Google Scholar
  93. 93.
    Binger P (1967) Angew Chem Int Ed 6:84Google Scholar
  94. 94.
    Pelter A, Harrison CR (1974) J Chem Soc Chem Commun 829Google Scholar
  95. 95.
    Naruse M, Utimoto K, Nozaki H (1974) Tetrahedron 30:3037Google Scholar
  96. 96.
    Suzuki A, Miyaura N, Abiko S, Itoh M, Brown HC, Sinclair JA, Midland MM (1973) J Am Chem Soc 95:3080Google Scholar
  97. 97.
    Naruse M, Utimoto K, Nozaki H (1973) Tetrahedron Lett 14:1847Google Scholar
  98. 98.
    Naruse M, Utimoto K, Nozaki H (1973) Tetrahedron 30:2159Google Scholar
  99. 99.
    Pelter A, Hughes L (1977) J Chem Soc Chem Commun 913Google Scholar
  100. 100.
    Pelter A, Gould KJ (1974) J Chem Soc Chem Commun 347Google Scholar
  101. 101.
    Hara S, Kishimura K, Suzuki A (1980) Chem Lett 9:221Google Scholar
  102. 102.
    Ishida N, Miura T, Murakami M (2007) Chem Commun 4381Google Scholar
  103. 103.
    Ishida N, Shimamoto Y, Murakami M (2010) Org Lett 12:3179Google Scholar
  104. 104.
    Ishida N, Narumi M, Murakami M (2012) Helv Chim Acta 95:474Google Scholar
  105. 105.
    Wakamiya A, Taniguchi T, Yamaguchi S (2006) Angew Chem Int Ed 45:3170Google Scholar
  106. 106.
    Yoshino J, Kano N, Kawashima T (2007) Chem Commun 559Google Scholar
  107. 107.
    Ishida N, Ikemoto W, Narumi M, Murakami M (2011) Org Lett 13:3008Google Scholar
  108. 108.
    Shimamoto Y, Sunaba H, Ishida N, Murakami M (2013) Eur J Org Chem 1421Google Scholar
  109. 109.
    Ishida N, Narumi M, Murakami M (2008) Org Lett 10:1279Google Scholar
  110. 110.
    Chen Y, Li N, Deng M (1990) Tetrahedron Lett 31:2405Google Scholar
  111. 111.
    Ishida N, Shinmoto T, Sawano S, Miura T, Murakami M (2010) Bull Chem Soc Jpn 83:1380Google Scholar
  112. 112.
    Fukushima M, Takushima D, Satomura H, Onodera G, Kimura M (2012) Chem Eur J 18:8019Google Scholar
  113. 113.
    Wrackmeyer B (1995) Coord Chem Rev 145:125Google Scholar
  114. 114.
    Kehr G, Erker G (2012) Chem Commun 48:1839Google Scholar
  115. 115.
    Wrackmeyer B, Nöth H (1976) J Organomet Chem 108:C21Google Scholar
  116. 116.
    Menz G, Wrackmeyer B (1977) Z Naturforsch 32b:1400Google Scholar
  117. 117.
    Chen C, Voss T, Fröhlich R, Kehr G, Erker G (2011) Org Lett 13:62Google Scholar
  118. 118.
    Köster R, Seidel G, Wrackmeyer B (1989) Chem Ber 122:1825Google Scholar
  119. 119.
    Ekkert O, Kehr G, Fröhlich R, Erker G (2011) J Am Chem Soc 133:4610Google Scholar
  120. 120.
    Wrackmeyer B, Horchler K, Boese R (1989) Angew Chem Int Ed 28:1500Google Scholar
  121. 121.
    Sebald A, Wrackmeyer B (1983) J Chem Soc Chem Commun 309Google Scholar
  122. 122.
    Chen C, Kehr G, Fröhlich R, Erker G (2010) J Am Chem Soc 132:13594Google Scholar
  123. 123.
    Fan C, Piers WE, Parves M, McDonald R (2010) Organometallics 29:5132Google Scholar
  124. 124.
    Ekkert O, Kehr G, Fröhlich R, Erker G (2011) Chem Commun 47:10482Google Scholar
  125. 125.
    Wrackmeyer B, Kehr G, Boese R (1991) Angew Chem Int Ed 30:1370Google Scholar
  126. 126.
    Killian L, Wrackmeyer B (1977) J Organomet Chem 132:213Google Scholar
  127. 127.
    Ge F, Kehr G, Daniliuc CG, Erker G (2014) J Am Chem Soc 136:68Google Scholar
  128. 128.
    Wrackmeyer B (1986) J Chem Soc Chem Commun 397Google Scholar
  129. 129.
    Wrackmeyer B (1986) J Organomet Chem 310:151Google Scholar
  130. 130.
    Wrackmeyer B, Pedall A, Weidinger J (2002) J Organomet Chem 649:225Google Scholar
  131. 131.
    Sebald A, Wrackmeyer B (1983) J Chem Soc Chem Commun 1293Google Scholar
  132. 132.
    Podiyanachari SK, Fröhlich R, Daniliuc CG, Petersen JL, Mück-Lichtenfeld C, Kehr G, Erker G (2012) Angew Chem Int Ed 51:8830Google Scholar
  133. 133.
    Ugolotti J, Kehr G, Fröhlich R, Erker G (2010) Chem Commun 46:3016Google Scholar
  134. 134.
    Ugolotti J, Dierker G, Kehr G, Fröhlich R, Grimme S, Erker G (2008) Angew Chem Int Ed 47:2622Google Scholar
  135. 135.
    Ugolotti J, Kehr G, Fröhlich R, Grimme S, Erker G (2009) J Am Chem Soc 131:1996Google Scholar

Copyright information

© Springer International Publishing Switzerland 2015

Authors and Affiliations

  1. 1.Department of Synthetic Chemistry and Biological ChemistryKyoto UniversityKatsuraJapan

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