4,4,6-Trimethyl-1,3,2-dioxaborinane: A Practical Reagent for Palladium-Catalyzed­ Borylation of Aryl Halides

Abstract

The palladium-catalyzed borylation of aryl iodides with 4,4,6-trimethyl-1,3,2-dioxaborinane is described. The mild reaction conditions employed allow for aryl iodides with a wide variety of functional groups to be tolerated. The products of this borylation were coupled with aryl halides to give biaryls in good yields.

boron - palladium - catalysis - cross-coupling - aryl halides

References and Notes

For reviews of the Suzuki coupling, see:

1a Miyaura N. Suzuki A. Chem. Rev.  1995,  95:  2457 

1b Miyaura N. Adv. Organomet. Chem.  1998,  6:  187 

1c Miyaura N. Top. Curr. Chem.  2002,  219:  11 

For reviews of the Miyaura borylation, see:

2a Ishiyama T. Miyaura N. J. Organomet. Chem.  2000,  611:  392 

2b Ishiyama T. Miyaura N. Chem. Rec.  2004,  3:  271 

3a Murata M. Watanabe S. Masuda Y. J. Org. Chem.  1997,  62:  6458 

3b Murata M. Oyama T. Watanabe S. Masuda Y. J. Org. Chem.  2000,  65:  164 

4a Murata M. Watanabe S. Masuda Y. Tetrahedron Lett.  2000,  41:  5877 

4b Murata M. Oyama T. Watanabe S. Masuda Y. Synthesis  2000,  778 

4c Murata M. Oyama T. Watanabe S. Masuda Y. Synth. Commun.  2002,  32:  2513 

5 Baudoin O. Guénard D. Guéritte F. J. Org. Chem.  2000,  65:  9268 

6 Wolan A. Zaidlewicz M. Org. Biomol. Chem.  2003,  1:  3274 

7 Broutin P.-E. Čerña I. Campaniello M. Leroux F. Colobert F. Org. Lett.  2004,  6:  4419 

8 Murata M. Sambommatsu T. Watanabe S. Masuda Y. Synlett  2006,  1867 

9 Tucker CE. Davidson J. Knochel P. J. Org. Chem.  1992,  57:  3482 

10a Woods WG. Strong PL. J. Am. Chem. Soc.  1966,  88:  4667 

10b Smith HD. Brotherton RJ. Inorg. Chem.  1970,  9:  2443 

11 Watanabe T. Miyaura N. Suzuki A. Synlett  1992,  207