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To "Rollover" or Not? Stereoelectronically Guided C-H Functionalization Pathways from Rhodium-Abnormal NHC
Champak Dutta1, Debasish Ghorai1, Joyanta Choudhury1
1Organometallics & Smart Materials Laboratory, Department of Chemistry, Indian Institute of Science Education and Research Bhopal, Bhopal 462066, India.
ACS Omega
|August 29, 2019
Summary
This study demonstrates selective control over rollover and nonrollover C-H activation pathways using rhodium(III)-abnormal N-heterocyclic carbene complexes. The findings enable precise functionalization of challenging chelating molecules via catalytic reactions.
Area of Science:
- Organometallic Chemistry
- Catalysis
- Organic Synthesis
Background:
- Rollover C-H activation is challenging for functionalizing reluctant chelating molecules.
- Selective C-H activation pathways depend on organometallic intermediate stereoelectronic properties.
Purpose of the Study:
- To achieve selective control over rollover versus nonrollover C-H activation pathways.
- To address C-H functionalization challenges using abnormal N-heterocyclic carbene (NHC) platforms.
Main Methods:
- Utilized rhodium(III)-abnormal NHC complexes.
- Employed catalytic reactions with pyridine-imidazolium substrates and internal alkynes.
Main Results:
- Successfully guided catalytic reactions toward selective rollover or nonrollover C-H functionalization.
- Demonstrated that steric and electronic demands dictate the reaction pathway.
Conclusions:
- Abnormal NHC ligands offer a platform for controlling C-H activation selectivity.
- This work provides a method for the targeted functionalization of complex molecules.