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
. 2013:4:531-535.
doi: 10.1039/c2sc21288a.

Divergent Reaction Pathways for Phenol Arylation by Arynes: Synthesis of Helicenes and 2-Arylphenols

Thanh Truong  1 , Olafs Daugulis
Affiliations

Divergent Reaction Pathways for Phenol Arylation by Arynes: Synthesis of Helicenes and 2-Arylphenols

Thanh Truong et al. Chem Sci. 2013.

Abstract

Two reactions of phenols with arynes have been developed. If LiTMP base is employed, arynes generated from aryl chlorides react with phenols to form helicenes. o-Arylation of phenols can be achieved by employing tBuONa base in the presence of AgOAc. Direct arylation of binol was achieved leading to the shortest pathway to o,o'-diarylbinols.

PubMed Disclaimer

Figures

Scheme 1
Scheme 1
Hexahelicene Synthesis
Scheme 2
Scheme 2
Reaction Intermediates
Scheme 3
Scheme 3
Reaction Mechanism
Scheme 4
Scheme 4
Binaphthol Arylation
See this image and copyright information in PMC

References

    1. Rueping M, Nachtsheim BJ, Koenigs RM, Ieawsuwan W. Chem.-Eur. J. 2010;16:13116. - PubMed
    2. Maeda H, Bando Y, Shimomura K, Yamada I, Naito M, Nobusawa K, Tsumatori H, Kawai T. J. Am. Chem. Soc. 2011;133:9266. - PubMed
    3. Englert M, Jolly PW, Wilke G. Angew. Chem., Int. Ed. 1971;10:77.
    4. Schuehly W, Paredes JMV, Kleyer J, Huefner A, Anavi-Goffer S, Raduner S, Altmann K-H, Gertsch J. Chem. Biol. 2011;18:1053. - PubMed
    1. Ackermann L, Kapdi AR, Fenner S, Kornhaaß C, Schulzke C. Chem.-Eur. J. 2011;17:2965. - PubMed
    1. Satoh T, Kawamura Y, Miura M, Nomura M. Angew. Chem., Int. Ed. 1997;36:1740.
    2. Bedford RB, Coles SJ, Hursthouse MB, Limmert ME. Angew. Chem., Int. Ed. 2003;42:112. - PubMed
    3. Bedford R, Webster RL, Mitchell CJ. Org. Biomol. Chem. 2009;7:4853. - PubMed
    4. Zhao X, Yeung CS, Dong VM. J. Am. Chem. Soc. 2010;132:5837. - PubMed
    5. Xiao B, Fu Y, Xu J, Gong T-J, Dai J-J, Yi J, Liu L. J. Am. Chem. Soc. 2010;132:468. - PubMed
    6. Huang C, Gevorgyan V. J. Am. Chem. Soc. 2009;131:10844. - PMC - PubMed
    7. Ciana C-L, Phipps RJ, Brandt JR, Meyer F-M, Gaunt MJ. Angew. Chem., Int. Ed. 2011;50:458. - PubMed
    8. Kirste A, Elsler B, Schnakenburg G, Waldvogel SR. J. Am. Chem. Soc. 2012;134:3571. - PubMed
    9. Ackermann L, Diers E, Manvar A. Org. Lett. 2012;14:1154. - PubMed
    10. Wetzel A, Pratsch G, Kolb R, Heinrich MR. Chem.-Eur. J. 2010;16:2547. Tritylaniline o-arylation by benzynes: - PubMed
    11. Pirali T, Zhang F, Miller AH, Head JL, McAusland D, Greaney M. Angew. Chem., Int. Ed. 2012;51:1006. - PubMed
    1. Huisgen R, Sauer J. Angew. Chem. 1960;72:91.
    1. Truong T, Daugulis O. J. Am. Chem. Soc. 2011;133:4243. - PMC - PubMed
    2. Truong T, Daugulis O. Org. Lett. 2011;13:4172. - PMC - PubMed
    3. Bajracharya G, Daugulis O. Org. Lett. 2008;10:4625. - PMC - PubMed

LinkOut - more resources