Synthesis 2016; 48(10): 1483-1490
DOI: 10.1055/s-0035-1561567
paper
© Georg Thieme Verlag Stuttgart · New York

Diastereoselective Pd-Catalyzed Domino Heck/Arylborylation Sequence Forming Borylated Chromans

Hyung Yoon
Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, M5S 3H6, Canada   Email: mlautens@chem.utoronto.ca
,
Young Jin Jang
Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, M5S 3H6, Canada   Email: mlautens@chem.utoronto.ca
,
Mark Lautens*
Davenport Research Laboratories, 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: 08 January 2016

Accepted: 14 January 2016

Publication Date:
07 March 2016 (online)


Abstract

A diastereoselective palladium-catalyzed domino Heck/arylborylation of aryl iodides yielding an alkylboronate containing a chroman is reported. The generated alkylpalladium(II) intermediate is intercepted with bis(pinacolato)diboron (B2pin2) in good yield as a single diastereomer.

Supporting Information