Pd/Cu-Catalyzed amide-enabled selectivity-reversed borocarbonylation of unactivated alkenes

The addition reaction between CuBpin and alkenes to give a terminal boron substituted intermediate is usually fast and facile. In this communication, a selectivity-reversed procedure has been designed and established. This selectivity-reversed borocarbonylation reaction is enabled by a cooperative a...

Full description

Saved in:
Bibliographic Details
Published in:Chemical science (Cambridge) 2021-08, Vol.12 (3), p.1341-1346
Main Authors: Wu, Fu-Peng, Wu, Xiao-Feng
Format: Article
Language:English
Subjects:
Alkenes
Chemistry
Copper
Crystallography
Iodides
Ketones
NMR
Nuclear magnetic resonance
Palladium
Regioselectivity
Selectivity
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The addition reaction between CuBpin and alkenes to give a terminal boron substituted intermediate is usually fast and facile. In this communication, a selectivity-reversed procedure has been designed and established. This selectivity-reversed borocarbonylation reaction is enabled by a cooperative action between palladium and copper catalysts and proceeds with complete regioselectivity. The key to the success of this transformation is the coordination of the amide group and slower CuBpin formation by using KHCO 3 as the base. A wide range of β-boryl ketones were produced from terminal unactivated aliphatic alkenes and aryl iodides. Further synthetic transformations of the obtained β-boryl ketones have been developed as well. A selectivity-reversed borocarbonylation reaction has been developed with complete regioselectivity.
ISSN:2041-6520
2041-6539
DOI:10.1039/d1sc02785a