Oxidative Annulation of Arenecarboxylic and Acrylic Acids with Alkynes under Ambient Conditions Catalyzed by an Electron-Deficient Rhodium(III) Complex

Eiji Kudo; Yu Shibata; Mutsumi Yamazaki; Koji Masutomi; Yuta Miyauchi; Miho Fukui; Haruki Sugiyama; Hidehiro Uekusa; Tetsuya Satoh; Masahiro Miura; Ken Tanaka

doi:10.1002/chem.201603499

Oxidative Annulation of Arenecarboxylic and Acrylic Acids with Alkynes under Ambient Conditions Catalyzed by an Electron-Deficient Rhodium(III) Complex

Chemistry. 2016 Sep 26;22(40):14190-4. doi: 10.1002/chem.201603499. Epub 2016 Aug 17.

Authors

Eiji Kudo¹, Yu Shibata², Mutsumi Yamazaki³, Koji Masutomi¹, Yuta Miyauchi¹, Miho Fukui^{1

3}, Haruki Sugiyama⁴, Hidehiro Uekusa⁴, Tetsuya Satoh^{5

6}, Masahiro Miura⁵, Ken Tanaka^{7

8}

Affiliations

¹ Department of Chemical Science and Engineering, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo, 152-8550, Japan.
² Department of Chemical Science and Engineering, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo, 152-8550, Japan. yshibata@apc.titech.ac.jp.
³ Department of Applied Chemistry, Graduate School of Engineering, Tokyo University of Agriculture and Technology, Koganei, Tokyo, 184-8588, Japan.
⁴ Department of Chemistry, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo, 152-8550, Japan.
⁵ Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka, 565-0871, Japan.
⁶ Department of Chemistry, Graduate School of Science, Osaka City University, 3-3-138 Sugimoto, Sumiyoshi-ku, Osaka, 558-8585, Japan.
⁷ Department of Chemical Science and Engineering, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo, 152-8550, Japan. ktanaka@apc.titech.ac.jp.
⁸ Department of Applied Chemistry, Graduate School of Engineering, Tokyo University of Agriculture and Technology, Koganei, Tokyo, 184-8588, Japan. ktanaka@apc.titech.ac.jp.

PMID: 27459131
DOI: 10.1002/chem.201603499

Abstract

It has been established that an electron-deficient Cp(E) rhodium(III) complex catalyzes the oxidative [4+2] annulation of substituted arenecarboxylic and acrylic acids with alkynes under ambient conditions (at RT-40 °C, under air) without using excess amounts of substrates to produce the corresponding substituted isocoumarins and α-pyrones in high yields. Minor modification of reaction conditions depending on the coordination ability of alkynes realized the high efficiency.

Keywords: alkynes; annulation; isocoumarins; rhodium; α-pyrones.