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

Hyung Yoon; Young Jin Jang; Mark Lautens

doi:10.1055/s-0035-1561567

Synthesis, Table of Contents

Synthesis 2016; 48(10): 1483-1490
DOI: 10.1055/s-0035-1561567

paper

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

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Abstract

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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.

Key words

palladium - Heck reaction - alkylboronate - diastereoselective - chroman - benzopyran

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References

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