Hydroboration of olefins with catecholborane at room temperature in the presence of N,N-dimethylacetamide

Journal of Organic Chemistry

Volumn 61, Issue 10, 1996, Pages 3224-3225

  Garrett, Christine E ^a   Fu, Gregory C ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0042103106     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960386p     Document Type: Article

References (38)

1. For leading references, see: (a) Pelter, A.; Smith, K.; Brown, H. C. Borane Reagents; Academic: New York, 1988. (b) Brown, H. C. Hlydroboration; W. A. Benjamin: New York, 1962.
2. For leading references, see: (a) Pelter, A.; Smith, K.; Brown, H. C. Borane Reagents; Academic: New York, 1988. (b) Brown, H. C. Hlydroboration; W. A. Benjamin: New York, 1962.
3. Brown, H. C.; Gupta, S. K. J. Am. Chem. Soc. 1975, 97, 5249-5255.
4. For overviews of the chemistry of catecholborane, including synthetic applications of B-alkylboronic esters, see: (a) Lane, C. F.; Kabalka, G. W. Tetrahedron 1976, 32, 981-990. (b) Kabalka, G. W. Org. Prep. Proc. Int. 1977, 9, 131-147. (c) Brown, H. C.; Chandrasekharan, J. J. Org. Chem. 1983, 48, 5080-5082. (d) VanNieuwenhze, M. S. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; Wiley: New York, 1995.
5. For overviews of the chemistry of catecholborane, including synthetic applications of B-alkylboronic esters, see: (a) Lane, C. F.; Kabalka, G. W. Tetrahedron 1976, 32, 981-990. (b) Kabalka, G. W. Org. Prep. Proc. Int. 1977, 9, 131-147. (c) Brown, H. C.; Chandrasekharan, J. J. Org. Chem. 1983, 48, 5080-5082. (d) VanNieuwenhze, M. S. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; Wiley: New York, 1995.
6. For overviews of the chemistry of catecholborane, including synthetic applications of B-alkylboronic esters, see: (a) Lane, C. F.; Kabalka, G. W. Tetrahedron 1976, 32, 981-990. (b) Kabalka, G. W. Org. Prep. Proc. Int. 1977, 9, 131-147. (c) Brown, H. C.; Chandrasekharan, J. J. Org. Chem. 1983, 48, 5080-5082. (d) VanNieuwenhze, M. S. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; Wiley: New York, 1995.
7. For overviews of the chemistry of catecholborane, including synthetic applications of B-alkylboronic esters, see: (a) Lane, C. F.; Kabalka, G. W. Tetrahedron 1976, 32, 981-990. (b) Kabalka, G. W. Org. Prep. Proc. Int. 1977, 9, 131-147. (c) Brown, H. C.; Chandrasekharan, J. J. Org. Chem. 1983, 48, 5080-5082. (d) VanNieuwenhze, M. S. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; Wiley: New York, 1995.
8. Mannig, D.; Noth, H. Angew. Chem., Int. Ed. Engl 1985, 24, 878-879.
9. For reviews, see: (a) Fu, G. C.; Evans, D. A.; Muci, A. R. In Advances in Catalytic Processes; Doyle, M. P., Ed.; JAI: Greenwich, CT, 1995; Vol. 1, pp 95-121. (b) Burgess, K.; Ohlmeyer, M. J. Chem. Rev. 1991, 91, 1179-1191.
10. For reviews, see: (a) Fu, G. C.; Evans, D. A.; Muci, A. R. In Advances in Catalytic Processes; Doyle, M. P., Ed.; JAI: Greenwich, CT, 1995; Vol. 1, pp 95-121. (b) Burgess, K.; Ohlmeyer, M. J. Chem. Rev. 1991, 91, 1179-1191.
11. 2) in a 2:1 ratio (cf. Mannig, D.; Noth, H. J. Chem. Soc., Dalton Trans. 1985, 1689-1692). Subsequent addition of 1-dodecene leads to the generation of tri(n-dodecyl)borane.
12. 2) in a 2:1 ratio (cf. Mannig, D.; Noth, H. J. Chem. Soc., Dalton Trans. 1985, 1689-1692). Subsequent addition of 1-dodecene leads to the generation of tri(n-dodecyl)borane.
13. For early work, see: (a) Burgess, K.; Ohlmeyer, M. J. J. Org. Chem. 1988, 53, 5178-5179. (b) Hayashi, T.; Matsumoto, Y.; Ito, Y. J. Am. Chem Soc. 1989, 111, 3426-3428.
14. For early work, see: (a) Burgess, K.; Ohlmeyer, M. J. J. Org. Chem. 1988, 53, 5178-5179. (b) Hayashi, T.; Matsumoto, Y.; Ito, Y. J. Am. Chem Soc. 1989, 111, 3426-3428.
15. 2O/1 N NaOH), the organic layer was dried, and the solvent was removed in vacuo. Flash chromatography afforded 0.184 g (96%) of 1- and 2-dodecanol in a 94:6 ratio (GC).
16. All reactions were conducted under an inert atmosphere with purified reagents (see the supporting information). However, in preliminary experiments we have found that the hydroboration of 1-dodecene proceeds equally smoothly when the reaction is run open to the air with unpurified reagents.
17. Control experiments for each reaction establish that <10% conversion is observed in the absence of N,N-dimethylacetamide under otherwise identical conditions.
18. 6.
19. This reaction also proceeds to completion in the presence of 1 mol % N,N-dimethylacetamide.
20. B-Alkylpinacolboranes are more stable to chromatography than are B-alkylcatecholboranes. For a recent discussion, see: Tucker, C. E.; Davidson, J.; Knochel, P. J. Org. Chem. 1992, 57, 3482-3485.
21. 3-THF promotes the addition of catecholborane to alkynes. (b) Dialkylborane: Arase, A.; Hoshi, M.; Mijin, A.; Nishi, K. Synth. Commun. 1995, 25, 1957-1962.
22. 3-THF promotes the addition of catecholborane to alkynes. (b) Dialkylborane: Arase, A.; Hoshi, M.; Mijin, A.; Nishi, K. Synth. Commun. 1995, 25, 1957-1962.
23. 3-THF promotes the addition of catecholborane to alkynes. (b) Dialkylborane: Arase, A.; Hoshi, M.; Mijin, A.; Nishi, K. Synth. Commun. 1995, 25, 1957-1962.
24. Transition metal complexes: (a) Westcott, S. A.; Blom, H. P.; Marder, T. B.; Baker, R. T. J. Am. Chem. Soc. 1992, 114, 8863-8869. (b) Burgess, K.; van der Donk, W. A.; Westcott, S. A.; Marder, T. B.; Baker, R. T.; Calabrese, J. C. J. Am. Chem. Soc. 1992, 114, 9350-9359. (c) Burgess, K.; Jaspars, M. Tetrahedron Lett. 1993, 34, 6813-6816. (d) Burgess, K.; Jaspars, M. Organametallics 1993, 12, 4197-4200. (e) Westcott, S. A.; Marder, T. B.; Baker, R. T.; Calabrese, J. C. Can. J. Chem. 1993, 71, 930-936. (f) Lindsley, C. W.; DiMare, M. Tetrahedron Lett. 1994, 35, 5141-5144. (g) Burgess, K.; van der Donk, W. A. Organometallics 1994, 13, 3616-3620. (h) Bijpost, E. A.; Duchateau, R.; Teuben, J. H J. Mol. Catal.: A 1995, 95, 121-128. (i) Reference 5a.
25. Transition metal complexes: (a) Westcott, S. A.; Blom, H. P.; Marder, T. B.; Baker, R. T. J. Am. Chem. Soc. 1992, 114, 8863-8869. (b) Burgess, K.; van der Donk, W. A.; Westcott, S. A.; Marder, T. B.; Baker, R. T.; Calabrese, J. C. J. Am. Chem. Soc. 1992, 114, 9350-9359. (c) Burgess, K.; Jaspars, M. Tetrahedron Lett. 1993, 34, 6813-6816. (d) Burgess, K.; Jaspars, M. Organametallics 1993, 12, 4197-4200. (e) Westcott, S. A.; Marder, T. B.; Baker, R. T.; Calabrese, J. C. Can. J. Chem. 1993, 71, 930-936. (f) Lindsley, C. W.; DiMare, M. Tetrahedron Lett. 1994, 35, 5141-5144. (g) Burgess, K.; van der Donk, W. A. Organometallics 1994, 13, 3616-3620. (h) Bijpost, E. A.; Duchateau, R.; Teuben, J. H J. Mol. Catal.: A 1995, 95, 121-128. (i) Reference 5a.
26. Transition metal complexes: (a) Westcott, S. A.; Blom, H. P.; Marder, T. B.; Baker, R. T. J. Am. Chem. Soc. 1992, 114, 8863-8869. (b) Burgess, K.; van der Donk, W. A.; Westcott, S. A.; Marder, T. B.; Baker, R. T.; Calabrese, J. C. J. Am. Chem. Soc. 1992, 114, 9350-9359. (c) Burgess, K.; Jaspars, M. Tetrahedron Lett. 1993, 34, 6813-6816. (d) Burgess, K.; Jaspars, M. Organametallics 1993, 12, 4197-4200. (e) Westcott, S. A.; Marder, T. B.; Baker, R. T.; Calabrese, J. C. Can. J. Chem. 1993, 71, 930-936. (f) Lindsley, C. W.; DiMare, M. Tetrahedron Lett. 1994, 35, 5141-5144. (g) Burgess, K.; van der Donk, W. A. Organometallics 1994, 13, 3616-3620. (h) Bijpost, E. A.; Duchateau, R.; Teuben, J. H J. Mol. Catal.: A 1995, 95, 121-128. (i) Reference 5a.
27. Transition metal complexes: (a) Westcott, S. A.; Blom, H. P.; Marder, T. B.; Baker, R. T. J. Am. Chem. Soc. 1992, 114, 8863-8869. (b) Burgess, K.; van der Donk, W. A.; Westcott, S. A.; Marder, T. B.; Baker, R. T.; Calabrese, J. C. J. Am. Chem. Soc. 1992, 114, 9350-9359. (c) Burgess, K.; Jaspars, M. Tetrahedron Lett. 1993, 34, 6813-6816. (d) Burgess, K.; Jaspars, M. Organametallics 1993, 12, 4197-4200. (e) Westcott, S. A.; Marder, T. B.; Baker, R. T.; Calabrese, J. C. Can. J. Chem. 1993, 71, 930-936. (f) Lindsley, C. W.; DiMare, M. Tetrahedron Lett. 1994, 35, 5141-5144. (g) Burgess, K.; van der Donk, W. A. Organometallics 1994, 13, 3616-3620. (h) Bijpost, E. A.; Duchateau, R.; Teuben, J. H J. Mol. Catal.: A 1995, 95, 121-128. (i) Reference 5a.
28. Transition metal complexes: (a) Westcott, S. A.; Blom, H. P.; Marder, T. B.; Baker, R. T. J. Am. Chem. Soc. 1992, 114, 8863-8869. (b) Burgess, K.; van der Donk, W. A.; Westcott, S. A.; Marder, T. B.; Baker, R. T.; Calabrese, J. C. J. Am. Chem. Soc. 1992, 114, 9350-9359. (c) Burgess, K.; Jaspars, M. Tetrahedron Lett. 1993, 34, 6813-6816. (d) Burgess, K.; Jaspars, M. Organametallics 1993, 12, 4197-4200. (e) Westcott, S. A.; Marder, T. B.; Baker, R. T.; Calabrese, J. C. Can. J. Chem. 1993, 71, 930-936. (f) Lindsley, C. W.; DiMare, M. Tetrahedron Lett. 1994, 35, 5141-5144. (g) Burgess, K.; van der Donk, W. A. Organometallics 1994, 13, 3616-3620. (h) Bijpost, E. A.; Duchateau, R.; Teuben, J. H J. Mol. Catal.: A 1995, 95, 121-128. (i) Reference 5a.
29. Transition metal complexes: (a) Westcott, S. A.; Blom, H. P.; Marder, T. B.; Baker, R. T. J. Am. Chem. Soc. 1992, 114, 8863-8869. (b) Burgess, K.; van der Donk, W. A.; Westcott, S. A.; Marder, T. B.; Baker, R. T.; Calabrese, J. C. J. Am. Chem. Soc. 1992, 114, 9350-9359. (c) Burgess, K.; Jaspars, M. Tetrahedron Lett. 1993, 34, 6813-6816. (d) Burgess, K.; Jaspars, M. Organametallics 1993, 12, 4197-4200. (e) Westcott, S. A.; Marder, T. B.; Baker, R. T.; Calabrese, J. C. Can. J. Chem. 1993, 71, 930-936. (f) Lindsley, C. W.; DiMare, M. Tetrahedron Lett. 1994, 35, 5141-5144. (g) Burgess, K.; van der Donk, W. A. Organometallics 1994, 13, 3616-3620. (h) Bijpost, E. A.; Duchateau, R.; Teuben, J. H J. Mol. Catal.: A 1995, 95, 121-128. (i) Reference 5a.
30. Transition metal complexes: (a) Westcott, S. A.; Blom, H. P.; Marder, T. B.; Baker, R. T. J. Am. Chem. Soc. 1992, 114, 8863-8869. (b) Burgess, K.; van der Donk, W. A.; Westcott, S. A.; Marder, T. B.; Baker, R. T.; Calabrese, J. C. J. Am. Chem. Soc. 1992, 114, 9350-9359. (c) Burgess, K.; Jaspars, M. Tetrahedron Lett. 1993, 34, 6813-6816. (d) Burgess, K.; Jaspars, M. Organametallics 1993, 12, 4197-4200. (e) Westcott, S. A.; Marder, T. B.; Baker, R. T.; Calabrese, J. C. Can. J. Chem. 1993, 71, 930-936. (f) Lindsley, C. W.; DiMare, M. Tetrahedron Lett. 1994, 35, 5141-5144. (g) Burgess, K.; van der Donk, W. A. Organometallics 1994, 13, 3616-3620. (h) Bijpost, E. A.; Duchateau, R.; Teuben, J. H J. Mol. Catal.: A 1995, 95, 121-128. (i) Reference 5a.
31. Transition metal complexes: (a) Westcott, S. A.; Blom, H. P.; Marder, T. B.; Baker, R. T. J. Am. Chem. Soc. 1992, 114, 8863-8869. (b) Burgess, K.; van der Donk, W. A.; Westcott, S. A.; Marder, T. B.; Baker, R. T.; Calabrese, J. C. J. Am. Chem. Soc. 1992, 114, 9350-9359. (c) Burgess, K.; Jaspars, M. Tetrahedron Lett. 1993, 34, 6813-6816. (d) Burgess, K.; Jaspars, M. Organametallics 1993, 12, 4197-4200. (e) Westcott, S. A.; Marder, T. B.; Baker, R. T.; Calabrese, J. C. Can. J. Chem. 1993, 71, 930-936. (f) Lindsley, C. W.; DiMare, M. Tetrahedron Lett. 1994, 35, 5141-5144. (g) Burgess, K.; van der Donk, W. A. Organometallics 1994, 13, 3616-3620. (h) Bijpost, E. A.; Duchateau, R.; Teuben, J. H J. Mol. Catal.: A 1995, 95, 121-128. (i) Reference 5a.
32. Transition metal complexes: (a) Westcott, S. A.; Blom, H. P.; Marder, T. B.; Baker, R. T. J. Am. Chem. Soc. 1992, 114, 8863-8869. (b) Burgess, K.; van der Donk, W. A.; Westcott, S. A.; Marder, T. B.; Baker, R. T.; Calabrese, J. C. J. Am. Chem. Soc. 1992, 114, 9350-9359. (c) Burgess, K.; Jaspars, M. Tetrahedron Lett. 1993, 34, 6813-6816. (d) Burgess, K.; Jaspars, M. Organametallics 1993, 12, 4197-4200. (e) Westcott, S. A.; Marder, T. B.; Baker, R. T.; Calabrese, J. C. Can. J. Chem. 1993, 71, 930-936. (f) Lindsley, C. W.; DiMare, M. Tetrahedron Lett. 1994, 35, 5141-5144. (g) Burgess, K.; van der Donk, W. A. Organometallics 1994, 13, 3616-3620. (h) Bijpost, E. A.; Duchateau, R.; Teuben, J. H J. Mol. Catal.: A 1995, 95, 121-128. (i) Reference 5a.
33. Phosphines: Westcott, S. A.; Blom, H. P.; Marder, T. B.; Baker, R. T.; Calabrese, J. C. Inorg. Chem. 1993, 32, 2175-2182.
34. 3-THF with N,N-dimethylacetamide.
35. 4, monoalkylboranes react with catecholborane to form B-alkylcatecholboranes (ref 15g).
36. 3-(N,N-diethylaniline)-catalyzed hydroboration of alkynes with catecholborane (ref 14a).
37. For a related observation, see: Brown, H. C.; Gupta, S. K. J. Am. Chem. Soc. 1971, 93, 1816-1818.
38. 4-catalyzed variant of eq 5 (ref 15g).