Recent developments in bisdiborane chemistry: B-C-B, B-C-C-B, B-C=C-B and B-C≡C-B compounds

Applied Organometallic Chemistry

Volumn 17, Issue 6-7, 2003, Pages 327-345

  Dembitsky, Valery M ^a   Ali, Hijazi Abu ^a   Srebnik, Morris ^a  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

Author keywords

1 alkynylboronates; Bis(boryl)alkenes; Bis(catecholato) diborane(4); Bis(pinacolato) diborane(4); Bisdiborane; Carbenoids; Diazoalkanes; Diboration; Dihydroboration; Geminated boranes; Hydroboration; Insertions; Tetraorganodiborane; Thermolysis; Vinylphosphonates

Indexed keywords

BISDIBORANE; BORANE DERIVATIVE; CARBON; UNCLASSIFIED DRUG;

CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; HYDROBORATION; ORGANIC CHEMISTRY; REACTION ANALYSIS; REVIEW; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0037762613     PISSN: 02682605     EISSN: None     Source Type: Journal    
DOI: 10.1002/aoc.430     Document Type: Review

References (116)

1. Urry G, Kerrigan J, Parsons TD, Schlesinger HI. J. Am. Chem. Soc. 1954; 76: 5299.
2. Onak T. Organoboron Chemistry. Academic Press: New York, 1975; 38-40.
3. Coyle TD, Ritter JJ. Adv. Organometal. Chem. 1972; 10: 237.
4. Muetterlies EL. The Chemistry of Boron and its Compounds. Wiley: New York, 1967; 398-399.
5. Abu Ali H, Goldberg I, Srebnik M. Eur. J. Inorg. Chem. 2002; 73.
6. Brotherton RJ, McCloskey JL, Petterson LL, Steinberg H. J. Am. Chem. Soc. 1960; 82: 6242.
7. Baker RT, Nguyen P, Marder TB, Westcott SA. Angew. Chem. Int. Ed. Engl. 1995; 34: 1336.
8. Ishiyama T, Yamamoto M, Miyaura N. Chem. Commun. 1997; 689.
9. Marder TB, Norman NC, Rice CR. Tetrahedron Lett. 1998; 39: 155.
10. Iverson CN, Smith MR. Organometallics 1997; 16: 2575.
11. Ishiyama T, Matsuda N, Murata M, Ozawa F, Suzuki A, Miyaura N. Organometallics 1996; 15: 713.
12. Iverson CN, Smith MR. J. Am. Chem. Soc. 1995; 117: 4403.
13. Cui Q, Musaev DGM, Morokuma K. Organometallics 1998; 17: 742.
14. Cui Q, Musaev DGM, Morokuma K. Organometallics 1998; 17: 1383.
15. Siebert W, Pritzkow H, Maderna A. Angew. Chem. Int. Ed. Engl. 1996; 35: 1501.
16. Clegg W, Scott AJ, Lesley G, Marder TB, Norman NC. Acta Crystallogr. Sect. C 1996; 52: 1989, 1991.
17. Nöth H. Z. Naturforsch. Teil B 1984; 39: 1463.
18. Lawlor FJ, Norman NC, Pickett NL, Robins EG. Inorg. Chem. 1998; 37: 1777.
19. Dembitsky VM, Tolstikov GA, Srebnik M. Eurasian Chem. Technol. J. 2002; 4: 87.
20. Corey EJ, Cheng X. The Logic of Chemical Synthesis. Wiley-Interscience: New York, 1989.
21. Wender PA (ed). Frontiers in Organic Synthesis thematic issue. Chem. Rev. 1996; 96: 1.
22. Dembitsky VM, Srebnik M. In Titanium and Zirconium in Organic Synthesis, Marek I (ed.). Wiley-VCH Verlag: Weinheim, 2002; 230-281.
23. Marek I. Chem. Rev. 2000; 100: 2887.
24. Binger P, Köster R. Angew. Chem. 1962; 7: 652.
25. Brown HC, Rhodes SP. J. Am. Chem. Soc. 1969; 91: 4306.
26. Zweifel G, Arzoumanian H. J. Am. Chem. Soc. 1967; 89: 291.
27. Zweifel G, Fischer RP, Horng A. Synthesis 1973; 37.
28. Ashe III AJ, Shu P. J. Am. Chem. Soc. 1971; 93: 1804.
29. Cainelli G, Dal Bello G, Zubiani G. Tetrahedron Lett. 1966; 4315.
30. Mukaiyama T, Murakami M, Oriyami T, Yamaguchi M. Chem. Lett. 1981; 1193.
31. Reddy CK, Periasamy M. Tetrahedron Lett. 1993; 49: 8877.
32. Abu Ali H, Goldberg I, Srebnik M. Organometallics 2001; 20: 3962.
33. Hooz J, Morrison GF. Can. J. Chem. 1970; 48: 868.
34. Hooz J, Gunn DM, Kono H. Can. J. Chem. 1971; 49: 2371.
35. Hooz J, Gunn DM. Tetrahedron Lett. 1969; 3455.
36. Ishiyama T, Momota S, Miyaura N. Synlett 1999; 11: 1790.
37. Abu Ali H, Goldberg I, Kaufmann D, Burmeister C, Srebnik M. Organometallics 2002; 21: 1870.
38. Wrackmeyer B, Kehr G. Polyhedron 1991; 10: 1497.
39. Herberich GE, Ohst H, Mayer H. Angew. Chem. Int. Ed. Engl. 1983; 23: 969.
40. Enders M, Pritzkow H, Siebert W. Angew. Chem. Int. Ed. Engl. 1992; 31: 606.
41. Eosch JJ. J. Organometal. Chem. 1995; 500: 101.
42. Wrackmeyer B, Kehr G. J. Organometal. Chem. 1995; 501: 87.
43. Greiwe P, Beez V, Pritzkow H, Siebert W. Eur. J. Inorg. Chem. 2001; 381.
44. Beez V, Greiwe P, Pritzkow H, Hofmann M, Schleyer PvR, Siebert W. Eur. J. Inorg. Chem. 1998; 1775.
45. Colberg JC, Rane A, Vaquer J, Soderquist JA. J. Am. Chem. Soc. 1993; 115: 6065.
46. Dulou R, Chretien-Bessiere Y. Bull. Soc. Chim. Fr. 1959; 1362.
47. Brown HC, Zweifel G. J. Am. Chem. Soc. 1961; 83: 3834.
48. Soundararajan R, Matteson DS. J. Org. Chem. 1990; 55: 2274.
49. Brown HC, Rhodes SP. J. Am. Chem. Soc. 1969; 91: 4306.
50. Zweifel G, Arzoumanian H. J. Am. Chem. Soc. 1967; 89: 291.
51. Cainelli G, Dal Bello G, Zubiani G. Tetrahedron Lett. 1965; 3429.
52. Binder P, Köster R. Angew. Chem. 1962; 74: 652.
53. Bubnov YuN, Bogdanov VS, Yakovlev IP, Mikhailov BM. Zh. Obsch. Khim. (SSSR) 1972; 42: 1313.
54. Kurahashi T, Hata T, Masai H, Kitagawa H, Shimizu M, Hiyama T. Tetrahedron 2002; 58: 6381.
55. Sakai M, Hayashi H, Miyaura N. Organometallics 1997; 16: 4229.
56. Castle RB, Matteson DS. J. Am. Chem. Soc. 1968; 90: 2194.
57. Castle RB, Matteson DS. J. Organometal. Chem. 1969; 20: 19.
58. Matteson DS, Wilcsek RJ. J. Organometal. Chem. 1973; 57: 231.
59. Matteson DS, Larson GL. J. Organometal. Chem. 1973; 57: 225.
60. Matteson DS, Thomas JR. J. Organometal. Chem. 1970; 24: 263.
61. Matteson DS, Tripathy PB. J. Organometal. Chem. 1970; 21: P6.
62. Matteson DS, Moody RJ. J. Am. Chem. Soc. 1977; 99: 3196.
63. Matteson DS. Stereodirected Synthesis with Organoboranes. Springer: Berlin, 1995.
64. Cainelli G, Dal Bello G, Zubiani G. Tetrahedron Lett. 1966; 4329.
65. Rathke MW, Kow R. J. Am. Chem. Soc. 1972; 94: 6854.
66. Kow R, Rathke MW. J. Am. Chem. Soc. 1973; 95: 2715.
67. Ashe AJ, Shu P. J Am. Chem. Soc. 1971; 93: 1804.
68. Matteson DS, Hagelee LA, Wilcsek RJ. J. Am. Chem. Soc. 1973; 95: 5096.
69. Matteson DS, Moody RJ. Organometallics 1982; 1: 20.
70. Soundararajan R, Matteson DS. Organometallics 1995; 14: 4157.
71. Jia L, Yang X, Stern CL, Marks TJ. Organometallics 1994; 13: 3755.
72. Parks DJ, Spence RE, Spence H, Piers WE. Angew. Chem. Int. Ed. Engl. 1995; 34: 809.
73. Kohler K, Piers WE, Jarvis AP, Xin S, Feng Y, Bravakis AM, Collins S, Clegg W, Yap GPA, Marder TB. Organometallics 1998; 17: 3557.
74. Piers WE, Irvine GJ, Williams VC. Eur. J. Inorg. Chem. 2000; 2131.
75. Marder TB, Norman NC. Top. Catal. 1998; 5: 63.
76. Abu Ali H, Goldberg I, Srebnik M. Organometallics 2001; 20: 3962.
77. Ziegler A, Pritzkow H, Siebert W. Eur. J. Inorg. Chem. 2001; 387.
78. Berndt A. Angew. Chem. Int. Ed. Engl. 1993; 32: 985.
79. Matteson DS, Majumdar D. J. Organometal. Chem. 1979; 170: 259.
80. Mikhailov BM, Bezmenov A, Vasil'ev LS, Kiselev VG. Dokl. Akad. Nauk SSSR 1964; 155: 141.
81. Mikhailov BM, Bezmenov A, Vasil'ev LS. Dokl. Akad. Nauk SSSR 1966; 167: 590.
82. Brown HC, Negishi E, Gupta SK. J. Am. Chem. Soc. 1970; 92: 2460.
83. Aronovich PM, Bogdanov VS, Mikhailov BM. Izv. Akad. Nauk SSSR Ser. Khim. 1969; 362.
84. Tanigawa Y, Moritaqni I, Nishida S. J. Organometal. Chem. 1971; 28: 73.
85. Matteson DS, Wilson JW. Organometallics 1985; 4: 1690.
86. Ishiyama T, Matsuda N, Miyaura N, Suzuki A. J. Am. Chem. Soc. 1993; 115: 11018.
87. Miyaura N, Suzuki A. Chem. Rev. 1995; 95: 2457.
88. Ishiyama T, Yamamoto M, Miyaura N. Chem. Lett. 1996; 1117.
89. Ishiyama T, Matsuda M, Murata M, Ozawa F, Suzuki A, Miyaura N. Organometallics 1996; 15: 713.
90. Binder P, Köster R. Tetrahedron Lett. 1965; 1901.
91. Lesley G, Nguyen P, Taylor J, Marder TB, Scott AJ, Clegg W, Norman NC. Organometallics 1996; 15: 5137.
92. Abu Ali H, Al Quntar AA, Goldberg I, Srebnik M. Organometallics 2002; 21: 4533.
93. Yang FY, Cheng CH. J. Am. Chem. Soc. 2001; 123: 761.
94. Iverson CN, Smith III MR. Organometallics 1997; 16: 2757.
95. Wiessauer C, Weissensteiner W. Tetrahedron Asymm. 1996; 7: 5.
96. Nguyen P, Coapes RB, Woodward AD, Taylor NJ, Burke JM, Howard JAK, Marder TB. J. Organometal. Chem. 2002; 652: 77.
97. Rudolph RW. J. Am. Chem. Soc. 1967; 89: 4216.
98. Zeldin M, Gatti AR, Wartik T. J. Am. Chem. Soc. 1967; 89: 4217.
99. Coyle TD, Ritter JJ. J. Am. Chem. Soc. 1967; 89: 5739.
100. Rozen A, Zeldin M. J. Organometal. Chem. 1971; 31: 319.
101. Eisch JJ, Gonsior LJ. J. Organometal. Chem. 1967; 8: 53.
102. Singleton DA, Redman AM. Tetrahedron Lett. 1994; 35: 509.
103. Corey EJ, Wollenberg RH. J. Am. Chem. Soc. 1974; 54: 5581.
104. Shriver DF, Biallas MJ. J. Am. Chem. Soc. 1967; 89: 1078.
105. Biallas MJ. J. Am. Chem. Soc. 1969; 91: 7290.
106. Biallas MJ. Inorg. Chem. 1971; 10: 1320.
107. Ceron P, Finch A, Frey J, Kerrigan J, Parsons T, Urry G, Schlesinger HI. J. Am. Chem. Soc. 1959; 81: 6368.
108. Kaufmann D. Chem. Ber. 1987; 120: 901.
109. Williams VC, Piers WE, Clegg W, Elsegood MRJ, Collins S, Marder TB. J. Am. Chem. Soc. 1999; 121: 3244.
110. Metz MV, Schwartz DJ, Stern CL, Nickias PN, Marks TJ. Angew. Chem. Int. Ed. Engl. 2000; 39: 1312.
111. Chambers D, Chivers T. J. Chem. Soc. 1964; 4782.
112. Metzler N, Nöth H, Thomann M. Organometallics 1993; 12: 2423.
113. Ester C, Madema A, Pritzkow H, Siebert W. Eur. J. Inorg. Chem. 2000; 1177.
114. Bluhm M, Madema A, Pritzkow H, Bethke S, Gleiter R, Siebert W. Eur. J. Inorg. Chem. 1999; 1693.
115. Eisch J, Kotowicz BW. Eur. J. Inorg. Chem. 1998; 761.
116. Ishiyama T, Miyaura N. J. Organometal. Chem. 2000; 611: 392.