Synthesis of aryl triolborates via nickel-catalyzed borylation of aryl halides with 5-(tert -Butyldimethylsiloxymethyl)-5-methyl-1,3,2-dioxaborinane

Synthesis

Volumn 44, Issue 8, 2012, Pages 1233-1236

  Sogabe, Yosuke ^a   Namikoshi, Takeshi ^a   Watanabe, Shinji ^a   Murata, Miki ^a  

^a KITAMI INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

aryl halides; carbon boron bond formation; cross coupling; hydroboranes; nickel catalysis

Indexed keywords

ARYL HALIDES; CARBON-BORON BONDS; CROSS-COUPLINGS; HYDROBORANES; NICKEL CATALYSIS;

BORON; CATALYSIS; FUNCTIONAL GROUPS;

METAL HALIDES;

5 (TERT BUTYLDIMETHYLSILOXYMETHYL) 5 METHYL 1,3,2 DIOXABORINANE; ARYLHALIDE; ARYLTRIOLBORATE; BORIC ACID; HALIDE; NICKEL; UNCLASSIFIED DRUG;

ARTICLE; BORYLATION; CATALYSIS; CHEMICAL COMPOSITION; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; SYNTHESIS;

EID: 84859615119     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0031-1289747     Document Type: Article

References (33)

1. Miyaura N, Suzuki A, Chem. Rev. 1995 95 2457
2. Kotha S, Lahiri K, Kashinath D, Tetrahedron 2002 58 9633
3. Martin R, Buchwald S L., Acc. Chem. Res. 2008 41 1461
4. Darses S, Genet J P., Chem. Rev. 2008 108 288
5. Yamamoto Y, Takizawa M, Yu X Q., Miyaura N, Angew. Chem. Int. Ed. 2008 47 928
6. Yu X Q., Yamamoto Y, Miyaura N, Chem.-Asian J. 2008 3 1517
7. Yu X Q., Yamamoto Y, Miyaura N, Synlett 2009 994
8. Yamamoto Y, Takizawa M, Yu X.-Q, Miyaura N, Heterocycles 2010 81 359
9. Yu X Q., Shirai T, Yamamoto Y, Miyaura N, Chem.-Asian J. 2011 3 932
10. Hall D G., In Boronic Acids Hall D G. Wiley-VCH Weinheim 2005 1
11. Ishiyama T, Miyaura N, In Boronic Acids Hall D G. Wiley-VCH Weinheim 2005 101
12. Merino P, Tejero T, Angew. Chem. Int. Ed. 2010 49 7164
13. Murata M, Watanabe S, Masuda Y, J. Org. Chem. 1997 62 6458
14. Murata M, Oyama T, Watanabe S, Masuda Y, J. Org. Chem. 2000 65 164
15. Baudoin O, Gunard D, Guritte F, J. Org. Chem. 2000 65 9268
16. Broutin P.-E, era I, Campaniello M, Leroux F, Colobert F, Org. Lett. 2004 6 4419
17. Murata M, Sambommatsu T, Watanabe S, Masuda Y, Synlett 2006 1867
18. Billingsley K L., Buchwald S L., J. Org. Chem. 2008 73 5589
19. Morgan A B., Jurs J L., Tour J M., J. Appl. Polym. Sci. 2000 76 1257
20. Rosen B M., Huang C, Percec V, Org. Lett. 2008 10 2597
21. Zhu W, Ma D, Org. Lett. 2006 8 261
22. Quite recently, Yamamoto et al. reported on transesterification of pinacol arylboronic esters with 1,1,1-tris(hydroxymethyl)ethane. They developed a one-pot procedure for the synthesis of aryl triolborates from aryl halides through palladium-catalyzed borylation with pinacolborane, see:, Li G.-Q, Kiyomura S, Yamamoto Y, Miyaura N, Chem. Lett. 2011 40 702
23. Our attempts to isolate 5-(hydroxymethyl)-5-methyl-1,3,2-dioxaborinane also failed. Furthermore, the use of 1,1,1-tris(hydroxymethyl)ethane instead of 1 for the one-pot nickel-catalyzed borylation was lacking in reactivity and reproducibility (0-50% yield).
24. Wilson D A., Wilson C J., Rosen B M., Percec V, Org. Lett. 2008 10 4879
25. Moldoveanu C, Wilson D A., Wilson C J., Corcoran P, Rosen B M., Percec V, Org. Lett. 2009 11 4974
26. Leowanawat P, Resmerita A M., Moldoveanu C, Liu C, Zhang N, Wilson D A., Hoang L M., Rosen B M., Percec V, J. Org. Chem. 2010 75 7822
27. Moldoveanu C, Wilson D A., Wilson C J., Leowanawat P, Resmerita A M., Liu C, Rosen B M., Percec V, J. Org. Chem. 2010 75 5438
28. Wilson D A., Wilson C J., Moldoveanu C, Resmerita A M., Corcoran P, Hoang L M., Rosen B M., Percec V, J. Am. Chem. Soc. 2010 132 1800
29. Murata M, Sambommatsu T, Oda T, Watanabe S, Masuda Y, Heterocycles 2010 80 213
30. Cunico R F., Bedell L, J. Org. Chem. 1980 45 4797
31. Corey E J., Venkateswarlu A, J. Am. Chem. Soc. 1972 94 6190
32. Van Hecke G R., Horrocks W D. Jr., Inorg. Chem. 1966 5 1968
33. McDougal P G., Rico J G., Oh Y I., Condon B D., J. Org. Chem. 1986 51 3388