Complete control of the chemoselectivity in catalytic carbene transfer reactions from ethyl diazoacetate: an N-heterocyclic carbene-Cu system that suppresses diazo coupling

Manuel R Fructos; Tomás R Belderrain; M Carmen Nicasio; Steven P Nolan; Harneet Kaur; M Mar Díaz-Requejo; Pedro J Pérez

doi:10.1021/ja047284y

Complete control of the chemoselectivity in catalytic carbene transfer reactions from ethyl diazoacetate: an N-heterocyclic carbene-Cu system that suppresses diazo coupling

J Am Chem Soc. 2004 Sep 8;126(35):10846-7. doi: 10.1021/ja047284y.

Authors

Manuel R Fructos¹, Tomás R Belderrain, M Carmen Nicasio, Steven P Nolan, Harneet Kaur, M Mar Díaz-Requejo, Pedro J Pérez

Affiliation

¹ Departamento de Química y Ciencia de los Materiales, Universidad de Huelva, Campus de El Carmen 21007-Huelva, Spain.

PMID: 15339161
DOI: 10.1021/ja047284y

Abstract

The complex IPrCuCl (1) catalyzes the transfer of the :CHCO2Et group from ethyl diazoacetate (EDA) to unsaturated and saturated substrates (olefins, amine, alcohols) with very high yields. In the absence of substrate, the complex 1 does not react with EDA to give the diazo coupling products (fumarate and maleate), a rare example in the field of metal-catalyzed diazocompounds decomposition.