Synthesis 2015; 47(16): 2446-2456
DOI: 10.1055/s-0034-1380198
special topic
© Georg Thieme Verlag Stuttgart · New York

Introduction of Hindered Electrophiles via C–H Functionalization in a Palladium-Catalyzed Multicomponent Domino Reaction

Zafar Qureshi
Davenport Research Laboratories, 80 St. George St., Toronto, ON, M5S 3H6, Canada   eMail: mlautens@chem.utoronto.ca
,
Waldemar Schlundt
Davenport Research Laboratories, 80 St. George St., Toronto, ON, M5S 3H6, Canada   eMail: mlautens@chem.utoronto.ca
,
Mark Lautens*
Davenport Research Laboratories, 80 St. George St., Toronto, ON, M5S 3H6, Canada   eMail: mlautens@chem.utoronto.ca
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Publikationsverlauf

Received: 23. Februar 2015

Accepted after revision: 14. März 2015

Publikationsdatum:
13. April 2015 (online)

Abstract

A general method for the incorporation of secondary alkyl iodides in a palladium-catalyzed multicomponent domino reaction is reported. With the relatively inexpensive Pd(OAc)2 as the catalyst and norbornene as a mediator, a variety of 1,2,3-trisubstituted aromatic compounds were synthesized. The reaction was shown to be scalable, producing excellent isolated yields on up to 5 mmol scale. Chiral alkyl iodides were also incorporated without any loss of stereochemical information. The developed method offers an expedient and mild C–H functionalization strategy for the synthesis of sterically congested aromatic compounds in a one-pot process.

Supporting Information

 
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