Synthesis 2016; 48(19): 3155-3164
DOI: 10.1055/s-0035-1561670
paper
© Georg Thieme Verlag Stuttgart · New York

Orthogonally Reacting Boron Coupling Reagents: A Novel Multicomponent-Multicatalytic Reaction [(MC)2R] of Dichlorovinylpyrazine

Jordan M. Rebelo
Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, M5S 3H6, Canada   Email: mlautens@chem.utoronto.ca
,
Steffen Kress
Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, M5S 3H6, Canada   Email: mlautens@chem.utoronto.ca
,
Adam A. Friedman
Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, M5S 3H6, Canada   Email: mlautens@chem.utoronto.ca
,
Mark Lautens*
Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, M5S 3H6, Canada   Email: mlautens@chem.utoronto.ca
› Author Affiliations
Further Information

Publication History

Received: 03 April 2016

Accepted after revision: 09 May 2016

Publication Date:
21 June 2016 (online)


Abstract

The results presented herein illustrate the feasibility of two orthogonally reacting boron coupling reagents as a new control strategy in multicomponent-multicatalytic reaction [(MC)2R] chemistry. A process employing dichlorovinylpyrazine merging the rhodium-catalyzed hydroarylation with the Suzuki coupling has been discovered. Three new bonds are formed in a one-pot, one-step process efficiently providing highly substituted diaza-dihydrodibenzoxepine products.

Supporting Information

 
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