Ti(OiPr)(4)/nBuLi: an attractive reagent system for [2+2+2] cyclotrimerisation reactions

Valentin A. Rassadin (1) , E. Nicolas (2) , Yvan Six (1)

1 DCSO - Laboratoire de synthèse organique
2 LCM - Laboratoire de chimie moléculaire

A convenient method for the [2+2+2] cyclotrimerisation of alkynes using Ti(OiPr)4/nBuLi is presented. Homotrimerisation of arylacetylenes proceeds within minutes with excellent regioselectivity. Moreover, the intermolecular construction of ABB heterotrimers can be achieved selectively from two different alkynes with similar electronic properties. The method is also suitable for the synthesis of pyridines.

Domains: Organic chemistry

Valentin A. Rassadin, E. Nicolas, Yvan Six. Ti(OiPr)(4)/nBuLi: an attractive reagent system for [2+2+2] cyclotrimerisation reactions. Chemical Communications, 2014, 50 (may), pp.7666-7669. ⟨10.1039/C4CC02698E⟩. ⟨hal-01057803⟩