Related Experiment Video
Updated: Mar 14, 2026

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
Ti(OiPr)4-Mediated Multicomponent Reactions Involving Triple Additions to Isonitrile Carbon Atoms
Francesco Foschi1, Torsten Roth1, Hubert Wadepohl1
1Anorganisch-Chemisches Institut, Universität Heidelberg , Im Neuenheimer Feld 270, 69120 Heidelberg, Germany.
Abstract:
Double addition of Grignard reagents to isonitriles was achieved in the presence of stoichiometric amounts of [Ti(OiPr)4]. Functionalized isonitrile components were obtained in situ via lithiation of chiral and achiral 2-oxazolines, and the resulting amidomethyltitanium intermediate further reacted with a range of electrophiles. The established multicomponent procedure gave rise to highly substituted 2-aminomorpholines, acyclic diamino alcohols, and prenylated amino alcohols via straightforward synthetic protocols.
Related Concept Videos
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction
Cycloaddition Reactions: Overview
Radical Reactivity: Intramolecular vs Intermolecular
Cycloaddition Reactions: MO Requirements for Thermal Activation
Conjugate Addition to α,β-Unsaturated Carbonyl Compounds
Conjugate Addition (1,4-Addition) vs Direct Addition (1,2-Addition)
Conjugate addition results in a thermodynamically stable product. The reaction retains the stronger C=O bond at the expense of the weaker C=C π bond. The process is slow as the β carbon is less electrophilic than the carbonyl carbon.
Direct addition products are...

