Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2009 Aug 12;131(31):10844-5.
doi: 10.1021/ja904791y.

TBDPS and Br-TBDPS protecting groups as efficient aryl group donors in Pd-catalyzed arylation of phenols and anilines

Chunhui Huang  1 , Vladimir Gevorgyan
Affiliations

TBDPS and Br-TBDPS protecting groups as efficient aryl group donors in Pd-catalyzed arylation of phenols and anilines

Chunhui Huang et al. J Am Chem Soc. .

Abstract

It is shown that the TBDPS protecting group can serve as an efficient phenyl group donor for o-bromophenols via Pd-catalyzed C-H arylation followed by a routine TBAF deprotection of the resulting silacycles. Employment of the newly designed Br-TBDPS protecting group in the same sequence allows for a facile introduction of a phenyl group at the ortho position of phenols and anilines. Alternatively, switching desilylation to oxidation in the last step allows the conversion of forming silacycles into valuable o-biphenols.

PubMed Disclaimer

References

    1. Hassan J, Sévignon M, Gozzi C, Schulz E, Lemaire M. Chem. Rev. 2002;102:1359. - PubMed

    1. For a general review, see for example: De Meijere A, Diederich F, editors. Metal-Catalyzed Cross-Coupling Reactions. 2nd ed. Weinheim: Wiley-VCH; 2004.

    1. For reviews, see: Alberico D, Scott ME, Lautens M. Chem. Rev. 2007;107:174. Seregin IV, Gevorgyan V. Chem. Soc. Rev. 2007;36:1173. Campeau L-C, Stuart DR, Fagnou K. Aldrich Chim. Acta. 2007;40:35. For representative works on biaryl formation, see: Campeau L-C, Parisien M, Fagnou K. J. Am. Chem. Soc. 2004;126:9186. Lafrance M, Rowley CN, Woo TK, Fagnou K. J. Am. Chem. Soc. 2006;128:8754. Park C-H, Ryabova V, Seregin IV, Sromek AW, Gevorgyan V. Org. Lett. 2004;6:1159. Lane BS, Brown MA, Sames D. J. Am. Chem. Soc. 2005;127:8050. Daugulis O, Zaitsev VG. Angew. Chem. Int. Ed. 2005;44:4046. Wang C, Piel I, Glorius F. J. Am. Chem. Soc. 2009;131:4194. Chiong HA, Pham Q-N, Daugulis O. J. Am. Chem. Soc. 2007;129:9879. Do H-Q, Kashif Khan RM, Daugulis O. J. Am. Chem. Soc. 2008;130:15185. Phipps RJ, Gaunt MJ. Science. 2009;323:1593. Stuart DR, Fagnou K. Science. 2007;316:1172. Deprez NR, Kalyani D, Krause A, Sanford MS. J. Am. Chem. Soc. 2006;128:4972. Berman AM, Lewis JC, Bergman RG, Ellman JA. J. Am. Chem. Soc. 2008;130:14926. Do H-Q, Daugulis O. J. Am. Chem. Soc. 2007;129:12404. Brasche G, García-Fortanet J, Buchwald SL. Org. Lett. 2008;10:2207. Ackermann L, Althammer A, Fenner S. Angew. Chem. Int. Ed. 2009;48:201. Miyasaka M, Fukushima A, Satoh T, Hirano K, Miura M. Chem. Eur. J. 2009;15:3674. Voutchkova A, Coplin A, Leadbeater NE, Crabtree RH. Chem. Commun. 2008:6312.

    1. For directed intermolecular arylation, see: Wang D-H, Mei T-S, Yu J-Q. J. Am. Chem. Soc. 2008;130:17676. Yang S, Li B, Wan X, Shi Z. J. Am. Chem. Soc. 2007;129:6066. Özdemir I, Demir S, Çetinkaya B, Gourlaouen C, Maseras F, Bruneau C, Dixneuf PH. J. Am. Chem. Soc. 2008;130:1156. Ackermann L. Top. Organomet. Chem. 2007;24:35. Norinder J, Matsumoto A, Yoshikai N, Nakamura E. J. Am. Chem. Soc. 2008;130:5858. Lazareva A, Daugulis O. Org. Lett. 2006;8:5211. Kametani Y, Satoh T, Miura M, Nomura M. Tetrahedron Lett. 2000;40:2655. Ackermann L, Vicente R, Althammer A. Org. Lett. 2008;10:2299.

    1. Boebel TA, Hartwig JF. J. Am. Chem. Soc. 2008;130:7534. - PubMed
    2. Pastine SJ, Gribkov DV, Sames D. J. Am. Chem. Soc. 2006;128:14220. - PubMed
    3. Maehara A, Tsurugi H, Satoh T, Miura M. Org. Lett. 2008;10:1159. - PubMed
    4. Giri R, Wasa M, Breazzano SP, Yu J-Q. Org. Lett. 2006;8:5685. - PubMed
    5. Zaitsev VG, Shabashov D, Daugulis O. J. Am. Chem. Soc. 2005;127:13154. - PubMed
    6. Giri R, Chen X, Yu J-Q. Angew. Chem. Int. Ed. 2005;44:2112. - PubMed

Publication types