Cp*Rh(III)-Catalyzed Cross-Coupling of Alkyltrifluoroborate with α-Diazomalonates for C(sp(3))-C(sp(3)) Bond Formation

Organic Letters
Yin-Suo Lu, Wing-Yiu Yu


A Cp*Rh(III)-catalyzed cross-coupling of alkyltrifluoroborate with α-diazomalonates was developed; the C(sp(3))-C(sp(3)) bond coupled products were formed in up to 97% yields. The reaction tolerates some useful functional groups, including ketone, ester, amide, ether, sulfonyl, and thiophene. Electrospray ionization mass spectrometry (ESI-MS) analysis revealed the formation of a distinct molecular species corresponding to σ-alkylrhodium(III) complexes. The successful diazo coupling reaction may be attributed to coordination of the amide group that promotes stability of the alkylrhodium(III) complex through the formation of a five-membered metallacycle.


Jul 21, 2001·The Journal of Organic Chemistry·R Prabharasuth, David L Van Vranken
Oct 11, 2001·Journal of the American Chemical Society·Matthew R NethertonG C Fu
Jan 20, 2005·Angewandte Chemie·Anja C Frisch, Matthias Beller
Feb 24, 2006·Journal of the American Chemical Society·Yike Ni, John Montgomery
Jan 30, 2007·Accounts of Chemical Research·Gary A Molander, Noel Ellis
Apr 20, 2007·Organic Letters·Sean K J Devine, David L Van Vranken
Jul 14, 2007·Journal of the American Chemical Society·Bunnai Saito, Gregory C Fu
Dec 22, 2007·Chemical Reviews·Sylvain Darses, Jean-Pierre Genet
Mar 29, 2008·The Journal of Organic Chemistry·Romas Kudirka, David L Van Vranken
Apr 9, 2008·Organic Letters·Gary A Molander, Daniel E Petrillo
Apr 12, 2008·Organic Letters·Sean K J Devine, David L Van Vranken
May 2, 2008·Journal of the American Chemical Society·Bunnai Saito, Gregory C Fu
Jan 29, 2009·Angewandte Chemie·Alena Rudolph, Mark Lautens
Jul 4, 2009·The Journal of Organic Chemistry·Gary A Molander, Ludivine Jean-Gérard
Sep 30, 2009·Chemical Reviews·Michael P DoyleLei Zhou
Sep 15, 2010·Journal of the American Chemical Society·Lei ZhouJianbo Wang
Oct 15, 2010·Chemistry : a European Journal·José BarluengaCarlos Valdés
Nov 17, 2010·Journal of the American Chemical Society·Deidre L SandrockGary A Molander
May 11, 2011·Journal of the American Chemical Society·Zhe LuGregory C Fu
Jul 26, 2011·Chemical Society Reviews·Nobuaki KambeJun Terao
Jul 26, 2011·Chemical Society Reviews·Zhihui Shao, Hongbin Zhang
May 31, 2012·Organic Letters·Avinash KhannaDavid L Van Vranken
Aug 7, 2012·Journal of the American Chemical Society·Wai-Wing ChanWing-Yiu Yu
Dec 5, 2012·Chemical Communications : Chem Comm·Ping-Xin ZhouYong-Min Liang
Mar 14, 2013·Chemical Communications : Chem Comm·Ping-Xin ZhouYong-Min Liang
Jul 31, 2013·Journal of the American Chemical Society·Zhuangzhi ShiFrank Glorius
Oct 4, 2014·Organic Letters·Eugene S GutmanDavid L Van Vranken
Dec 2, 2014·The Journal of Organic Chemistry·Ying XiaJianbo Wang
Feb 12, 2015·Organic Letters·Ying XiaJianbo Wang
Mar 12, 2015·The Journal of Organic Chemistry·Jayanta Ghorai, Pazhamalai Anbarasan
Jun 20, 2015·The Journal of Organic Chemistry·Jack Chang Hung LeeDennis G Hall
Aug 19, 2015·Chemical Reviews·Alan FordM Anthony McKervey
Sep 17, 2015·Organic Letters·Arindam DasKálmán J Szabó


Jan 31, 2020·Chemistry : a European Journal·Amanda F da SilvaIgor D Jurberg

Related Concepts

Related Feeds

Birth Defects

Birth defects encompass structural and functional alterations that occur during embryonic or fetal development and are present since birth. The cause may be genetic, environmental or unknown and can result in physical and/or mental impairment. Here is the latest research on birth defects.