A Diels-Alder reaction triggered by a [4 + 3] metallacycloaddition

Journal of the American Chemical Society
Ángela VivancosEleuterio Álvarez

Abstract

The Tp(Me2)Ir(III) complex 1-OH2 (Tp(Me2) = hydrotris(3,5-dimethylpyrazolyl)borate), which contains a labile molecule of water and an iridium-bonded alkenyl moiety (-C(R)═C(R)-(R=CO2Me)) as part of a benzo-annulated five-membered iridacycle, reacts readily with the conjugated dienes butadiene and 2,3-dimethylbutadiene to afford the corresponding Diels-Alder products. Experimental and DFT studies are in accordance with an initial [4 + 3] cyclometalation reaction between the diene and the five-coordinated 16-electron organometallic fragment 1 (generated from 1-OH2 by facile water dissociation). The reaction can be extended to a related TpIr(III) complex (Tp = hydrotris(pyrazolyl)borate) that also features a labile ligand (i.e., 2-THF).

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Citations

Jan 26, 2017·Chemical Society Reviews·Wangyang MaZhenfeng Xi
Jul 8, 2015·Dalton Transactions : an International Journal of Inorganic Chemistry·Judith P Morales-CerónJosé M Vásquez-Pérez
Dec 6, 2017·Nature Communications·Qingde ZhuoHaiping Xia
Jan 24, 2019·Chemistry : a European Journal·Yongliang ZhangZhenfeng Xi
Jan 30, 2019·Chemistry : a European Journal·Jinhua LiHaiping Xia
Oct 18, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Giuseppe SciortinoPietro Vidossich

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