Reactions of arynes promoted by silver ions

Chemical Society Reviews
Rajdip Karmakar, Daesung Lee

Abstract

Arynes are unique aromatic species that display versatile reactivity in a variety of transformations. It has been demonstrated that the reaction profiles of arynes can be altered by transition metal additives, and one of the earliest examples of the metal additive effect was observed with silver ions (Ag(+)). Especially, in the presence of Ag(+), benzyne showed distinctive reactivity and selectivity toward π-nucleophiles compared to the corresponding reaction in its absence. Although more experimental data need to be accumulated to accurately define the Ag(+) additive effect, based on its role displayed in various transformations, we can infer that Ag(+) interacts with arynes to form a reactive intermediate, which behaves like a silver-bound aryl cation or 1,2-carbene-silver carbenoid. In this tutorial review, various aryne-mediated reactions involving Ag(+) or other organosilver species are discussed, which show a bird's-eye view on the Ag(+) effect in aryne chemistry such that further explorations of the unique reactivity of arynes under the influence Ag(+) will be inspired.

References

Jan 17, 2002·Journal of the American Chemical Society·Pankaj D RegeNancy S Goroff
Mar 17, 2012·Angewandte Chemie·Christian M Gampe, Erick M Carreira
Mar 27, 2012·Chemical Reviews·Pamela M Tadross, Brian M Stoltz
Oct 13, 2012·Nature·Thomas R HoyeBrian P Woods
Nov 8, 2012·Organic & Biomolecular Chemistry·Anton V DubrovskiyRichard C Larock
Feb 13, 2013·Journal of the American Chemical Society·Yuwen ZengJinbo Hu
Mar 13, 2013·Journal of the American Chemical Society·Sang Young YunDaesung Lee
Apr 2, 2013·Organic Letters·Rajdip KarmakarDaesung Lee
Feb 15, 2014·Journal of the American Chemical Society·Adam E GoetzNeil K Garg
Mar 4, 2014·Journal of the American Chemical Society·Nam-Kyu LeeYuanzhi Xia
May 2, 2014·Chemistry : a European Journal·Yuwen Zeng, Jinbo Hu
May 7, 2014·Angewandte Chemie·Catherine Holden, Michael F Greaney
Oct 11, 2014·Journal of the American Chemical Society·Jose M MedinaK N Houk
Sep 4, 2015·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Rajdip KarmakarDaesung Lee

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Citations

Oct 1, 2015·Genes, Brain, and Behavior·T T-Y LeeF S Lee
Nov 23, 2016·Chemistry : a European Journal·Sam G MossJoseph B Sweeney
Oct 19, 2016·Chemical Society Reviews·José-Antonio García-López, Michael F Greaney
May 26, 2018·Chemistry : a European Journal·Akira YoshimuraViktor V Zhdankin
Oct 6, 2017·Chemistry : a European Journal·Akira YoshimuraViktor V Zhdankin
Sep 3, 2019·Chemical Communications : Chem Comm·Sheng-Jun LiShi-Kai Tian
May 16, 2020·Chemical Communications : Chem Comm·Ruixiang ChengHuanfeng Jiang
Aug 29, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Hideto Miyabe
Jan 11, 2019·Chemical Science·Xinkan Yang, Gavin Chit Tsui
Oct 26, 2018·Chemical Society Reviews·Hiroshi TakikawaKeisuke Suzuki
Jun 20, 2020·Chemical Communications : Chem Comm·Tianhao LuChunsong Xie
Nov 21, 2020·Chemical Communications : Chem Comm·Liangliang YaoYimin Hu
Feb 19, 2021·Chemical Reviews·Jiarong ShiYang Li
Jul 9, 2021·Journal of the American Chemical Society·Jiarong ShiYang Li
Mar 2, 2017·The Journal of Organic Chemistry·Takashi IkawaShuji Akai
Feb 2, 2018·Organic Letters·Xinkan Yang, Gavin Chit Tsui
Jul 3, 2019·The Journal of Organic Chemistry·Jie ZhaoLei Wang
Nov 8, 2017·Accounts of Chemical Research·Samuel J HeinWilliam R Dichtel
Oct 5, 2018·Journal of the American Chemical Society·Dachuan QiuYang Li
Jul 3, 2018·Organic Letters·Rajdip KarmakarDaesung Lee
Nov 6, 2018·Journal of the American Chemical Society·Hang ShenThomas R Hoye
Jan 28, 2020·Accounts of Chemical Research·Jia HeYang Li

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