α-Hydroxymethylation of pyridines at a frustrated Lewis pair template

Muhammad Sajid; Gerald Kehr; Constantin G Daniliuc; Gerhard Erker

doi:10.1002/chem.201405553

α-Hydroxymethylation of pyridines at a frustrated Lewis pair template

Chemistry. 2015 Jan 19;21(4):1454-7. doi: 10.1002/chem.201405553. Epub 2014 Dec 2.

Authors

Muhammad Sajid¹, Gerald Kehr, Constantin G Daniliuc, Gerhard Erker

Affiliation

¹ Organisch-Chemisches Institut, Westfälische Wilhelms-Universität, Corrensstr. 40, 48149 Münster (Germany).

PMID: 25469672
DOI: 10.1002/chem.201405553

Abstract

The "η(2)-formylborane" moiety formed by CO reduction with HB(C6F5)2 at a P/B frustrated Lewis pair template undergoes a hydroxymethylation reaction at the α-position to nitrogen in pyridine or isoquinoline. The analogous reaction with pyrimidine revealed a mechanism related to the Tschitschibabin reaction.

Keywords: boron; frustrated Lewis pairs; hydroxymethylation; phosphorus; pyridine.