Journal
CHEMICAL RECORD
Volume 21, Issue 12, Pages 3613-3627Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/tcr.202100117
Keywords
bidentate directing group; regioselectivity; stereoselectivity; chiral auxiliary; C-H functionalization
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Funding
- Institute for Basic Science [IBS R010-A2]
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This article highlights the elegant and versatile approach of chelation-assisted C-H bond and alkene functionalization using bidentate directing groups, which overcomes regiocontrol issues. The focus is on two categories of results: regioselective alkene functionalization and asymmetric C-H functionalization using chiral bidentate directing groups. Additionally, density functional theory studies are discussed to elucidate the origin of regio- and stereoselectivity induced by bidentate directing groups.
Chelation-assisted C-H bond and alkene functionalization using bidentate directing groups offers an elegant and versatile approach to overcome regiocontrol issues by allowing the catalyst to come into close proximity with the targeted sites. In this personal account, we highlight our recent works in developing regio- and stereocontrolled functionalizations through transition-metal catalysis enabled by bidentate directing groups. We classify our results into two categories: (1) regioselective alkene functionalization using bidentate directing groups, and (2) asymmetric C-H functionalization using chiral bidentate directing groups. Furthermore, density functional theory studies to elucidate the origin of the regio- and stereoselectivity exerted by bidentate directing groups are discussed.
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