Regioselective C-H activation and sequential C-C and C-O bond formation reactions of aryl ketones promoted by an yttrium carbene

David P Mills; Lyndsay Soutar; William Lewis; Alexander J Blake; Stephen T Liddle

doi:10.1021/ja107958u

Regioselective C-H activation and sequential C-C and C-O bond formation reactions of aryl ketones promoted by an yttrium carbene

J Am Chem Soc. 2010 Oct 20;132(41):14379-81. doi: 10.1021/ja107958u.

Authors

David P Mills¹, Lyndsay Soutar, William Lewis, Alexander J Blake, Stephen T Liddle

Affiliation

¹ School of Chemistry, University of Nottingham, University Park, Nottingham, NG7 2RD, UK.

PMID: 20873758
DOI: 10.1021/ja107958u

Abstract

Rare earth carbenes exclusively exhibit Wittig-type reactivity with carbonyl compounds to afford alkenes. Here, we report that yttrium carbenes can effect regioselective ortho-C-H activation and sequential C-C and C-O bond formation reactions of aryl ketones to give iso-benzofurans and hydroxymethylbenzophenones. With MeCOPh, cyclotetramerization occurs giving a substituted cyclohexene. This demonstrates new rare earth carbene reactivity which complements existing Wittig-type reactivity.