Practical radical cyclizations with arylboronic acids and trifluoroborates

Jonathan W Lockner; Darryl D Dixon; Rune Risgaard; Phil S Baran

doi:10.1021/ol2023505

Practical radical cyclizations with arylboronic acids and trifluoroborates

Org Lett. 2011 Oct 21;13(20):5628-31. doi: 10.1021/ol2023505. Epub 2011 Sep 16.

Authors

Jonathan W Lockner¹, Darryl D Dixon, Rune Risgaard, Phil S Baran

Affiliation

¹ Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.

Abstract

Practical radical cyclizations using organoboronic acids and trifluoroborates take place in water, open to air, and in a scalable fashion employing catalytic silver nitrate and stoichiometric potassium persulfate. Both Pschorr-type cyclizations and tandem radical cyclization/trap cascades are described, illustrating the utility of these mild conditions for the generation of polycyclic scaffolds.

Publication types

Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't

MeSH terms

Borates / chemistry*
Boronic Acids / chemistry*
Catalysis
Cyclization
Hydrocarbons, Fluorinated / chemistry*
Molecular Structure
Polycyclic Aromatic Hydrocarbons / chemical synthesis*
Polycyclic Aromatic Hydrocarbons / chemistry
Water / chemistry

Substances

Borates
Boronic Acids
Hydrocarbons, Fluorinated
Polycyclic Aromatic Hydrocarbons
Water

Abstract

Publication types

MeSH terms

Substances

Grants and funding