Platinum- and gold-catalyzed hydrative carbocyclization of oxo diynes for one-pot synthesis of benzopyrones and bicyclic spiro ketones

Organic Letters
Arindam DasRai-Shung Liu

Abstract

We report a one-pot synthesis of benzopyrones and tricyclic spiroketones from hydrative carbocyclization of oxodiyne substrates catalyzed by PtCl2 and PPh3AuCl/AgOTf, respectively. The distinct carbocyclizations with Pt and Au catalysts stem from their altered regioselectivity in the oxo-assisted hydration of the neighboring alkyne carbons.

References

Oct 24, 2002·Journal of the American Chemical Society·Naoki AsaoYoshinori Yamamoto
Feb 20, 2003·Journal of the American Chemical Society·Hua Qian, Ross A Widenhoefer
Sep 18, 2003·Journal of the American Chemical Society·Barry M Trost, Michael T Rudd
Apr 9, 2004·Journal of the American Chemical Society·Joshua J Kennedy-SmithF Dean Toste
Oct 7, 2004·Angewandte Chemie·Steven T StabenF Dean Toste
Mar 31, 2005·Journal of the American Chemical Society·Barry M Trost, Michael T Rudd
Jun 9, 2005·Journal of the American Chemical Society·Alois FürstnerTobias Gress
Sep 1, 2005·Journal of the American Chemical Society·Yiyun ChenChulbom Lee
Oct 27, 2005·Journal of the American Chemical Society·Alois Fürstner, Paul W Davies
Dec 8, 2005·Journal of the American Chemical Society·Britton K Corkey, F Dean Toste
Feb 24, 2006·Organic Letters·Bhanu Pratap TaduriRai-Shung Liu
Oct 10, 2006·The Journal of Organic Chemistry·Sachin Madan, Chien-Hong Cheng
Dec 16, 2006·The Journal of Organic Chemistry·Fujiko KonnoKentaro Yamaguchi

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Citations

Mar 9, 2017·The Journal of Organic Chemistry·Bhornrawin AkkachairinSomsak Ruchirawat
Dec 17, 2009·Angewandte Chemie·Nicholas A Afagh, Andrei K Yudin
Feb 15, 2017·Angewandte Chemie·Thomas WurmA Stephen K Hashmi
Jan 27, 2018·Chemistry : a European Journal·Vanessa WeingandA Stephen K Hashmi
Jun 16, 2016·Organic & Biomolecular Chemistry·A Leela Siva KumariK C Kumara Swamy
Oct 8, 2016·Organic & Biomolecular Chemistry·Tanmoy Chanda, Maya Shankar Singh
May 26, 2010·Organic & Biomolecular Chemistry·Paul W Davies, Christelle Detty-Mambo
Sep 27, 2014·Organic & Biomolecular Chemistry·Chandrasekhar ChallaRavi S Lankalapalli
Jun 15, 2011·Angewandte Chemie·David LebœufLouis Fensterbank
Jul 8, 2016·Chemical Society Reviews·Abdullah M Asiri, A Stephen K Hashmi
May 19, 2021·The Journal of Physical Chemistry. a·Tarun RoyVenkatesan S Thimmakondu
Jun 25, 2021·Organic & Biomolecular Chemistry·Charnsak ThongsornkleebSomsak Ruchirawat
Mar 12, 2011·Chemical Reviews·A CormaMaria J Sabater
Apr 14, 2015·Journal of the American Chemical Society·Stefan Diethelm, Erick M Carreira
Jun 6, 2012·Journal of the American Chemical Society·Weidong RaoPhilip Wai Hong Chan
Aug 25, 2011·Journal of the American Chemical Society·Hang ShiZhen Yang
May 1, 2013·Journal of the American Chemical Society·Weidong RaoPhilip Wai Hong Chan
Apr 7, 2015·Chemical Reviews·Ruth Dorel, Antonio M Echavarren

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