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Paper | Regular issue | Vol 98, No. 4, 2019, pp.519-533
Published online, 27th March, 2019
DOI: 10.3987/COM-19-14064
The Use of Formaldehyde in the Rhodium-Catalyzed Linear-Selective Hydroformylation of Vinylheteroarenes

Jian Pan, Tsumoru Morimoto,* Hideyuki Kobayashi, Hiroki Tanimoto, and Kiyomi Kakiuchi

*Division of Materials Science, Nara Institute of Science and Technology, 8916-5 Takayama, Ikoma, Nara 630-0192, Japan

Abstract

An accessible protocol for the linear-selective hydroformylation of vinylheteroarenes using formaldehyde as a substitute for syngas is reported. The simultaneous use of BIPHEP and Nixantphos ligands permitted a high regioselectivity (linear/branched = up to 93/7) and moderate yield of isolated product (up to 84%) to be obtained. Under such catalytic conditions, vinylheteroarenes containing a vinyl group at the 2-position in the heterocycle ring reacted more linear-selectively with formaldehyde than at the 3-position.