Synlett 2018; 29(10): 1307-1313
DOI: 10.1055/s-0036-1591841
letter
© Georg Thieme Verlag Stuttgart · New York

Activation of Michael Acceptors by Halogen-Bond Donors

Daniel von der Heiden
Department für Chemie, Universität zu Köln, Greinstraße 4, 50939 Köln, Germany   Email: mbreugst@uni-koeln.de
,
Eric Detmar
Department für Chemie, Universität zu Köln, Greinstraße 4, 50939 Köln, Germany   Email: mbreugst@uni-koeln.de
,
Robert Kuchta
Department für Chemie, Universität zu Köln, Greinstraße 4, 50939 Köln, Germany   Email: mbreugst@uni-koeln.de
,
Department für Chemie, Universität zu Köln, Greinstraße 4, 50939 Köln, Germany   Email: mbreugst@uni-koeln.de
› Author Affiliations

Financial support from the Fonds der Chemischen Industrie (Liebig scholarship to M.B. and Ph.D. scholarships to D.v.d.H.) is gratefully acknowledged.
Further Information

Publication History

Received: 08 September 2017

Accepted after revision: 03 November 2017

Publication Date:
01 December 2017 (online)


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Published as part of the Special Section 9th EuCheMS Organic Division Young Investigator Workshop

In memoriam Professor J. Peter Guthrie

Abstract

Extending earlier studies on iodine catalysis, experimental investigations show that various halogen-bond donors can also be employed to accelerate the Michael addition between trans-crotonophenone and indole. Solvent as well as counteranion effects have been analyzed, and kinetic and computational investigations provide additional insights into the mode of activation.

Supporting Information