Additive Effects in the Palladium-Catalyzed Carboiodination of Chiral N-Allyl Carboxamides†
David A. Petrone
Department of Chemistry, University of Toronto, 80 St. George St. Toronto, Ontario (Canada) http://www.chem.utoronto.ca/staff/ML/index.php
Search for more papers by this authorHyung Yoon
Department of Chemistry, University of Toronto, 80 St. George St. Toronto, Ontario (Canada) http://www.chem.utoronto.ca/staff/ML/index.php
Search for more papers by this authorDr. Harald Weinstabl
Department of Chemistry, University of Toronto, 80 St. George St. Toronto, Ontario (Canada) http://www.chem.utoronto.ca/staff/ML/index.php
Search for more papers by this authorCorresponding Author
Prof. Dr. Mark Lautens
Department of Chemistry, University of Toronto, 80 St. George St. Toronto, Ontario (Canada) http://www.chem.utoronto.ca/staff/ML/index.php
Department of Chemistry, University of Toronto, 80 St. George St. Toronto, Ontario (Canada) http://www.chem.utoronto.ca/staff/ML/index.phpSearch for more papers by this authorDavid A. Petrone
Department of Chemistry, University of Toronto, 80 St. George St. Toronto, Ontario (Canada) http://www.chem.utoronto.ca/staff/ML/index.php
Search for more papers by this authorHyung Yoon
Department of Chemistry, University of Toronto, 80 St. George St. Toronto, Ontario (Canada) http://www.chem.utoronto.ca/staff/ML/index.php
Search for more papers by this authorDr. Harald Weinstabl
Department of Chemistry, University of Toronto, 80 St. George St. Toronto, Ontario (Canada) http://www.chem.utoronto.ca/staff/ML/index.php
Search for more papers by this authorCorresponding Author
Prof. Dr. Mark Lautens
Department of Chemistry, University of Toronto, 80 St. George St. Toronto, Ontario (Canada) http://www.chem.utoronto.ca/staff/ML/index.php
Department of Chemistry, University of Toronto, 80 St. George St. Toronto, Ontario (Canada) http://www.chem.utoronto.ca/staff/ML/index.phpSearch for more papers by this authorWe thank the Natural Sciences and Engineering Research Council of Canada (NSERC), the University of Toronto, and Alphora Inc. for financial support. M.L. thanks the Canada Council for the Arts for a Killam Fellowship. D.A.P. thanks NSERC for a postgraduate scholarship (CGS-D). H.W. thanks the Austrian Science Fund (FWF) (J3250-N19) for an Erwin Schrödinger postdoctoral fellowship. The authors wish to acknowledge CFI project number 19119 for funding the CSICOMPNMR Facility. Dr. Darcy Burns (Chemistry Department, U of T) is sincerely thanked for his intuitive assistance with NMR. Dr. Alan Lough (Chemistry Department, U of T) is thanked for single-crystal X-ray structural analysis. We thank Johnson Matthey for kind gifts of [Pd(QPhos)2]. Theo Bruun (U of T) is thanked for assistance in preparing starting materials for the racemic assays.
Abstract
The use of Pd catalysis as a means to synthesize organic halides has recently received increased attention. Among the reported methods is the Pd-catalyzed carboiodination, which uses extremely bulky ligands to facilitate carbon–halogen reductive elimination from PdII as the key catalytic step. When approaching substrates exhibiting low stereoselectivity, catalyst troubleshooting becomes difficult as there are few ligands known to promote the key reductive elimination. Herein, we present our finding that tertiary amines act as weakly coordinating ligands which significantly enhance diastereoselectivity in the Pd/QPhos-catalyzed carboiodination of chiral N-allyl carboxamides. This methodology allows efficient access to enantioenriched and densely functionalized dihydroisoquinolinones, and has been applied toward the asymmetric formal synthesis of (+)-corynoline.
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