Journal
ACS CATALYSIS
Volume 8, Issue 3, Pages 2166-2172Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.7b04395
Keywords
alkynylation; rhodium catalysis; C-H functionalization; inverse Sonogashira; metallacycle; Hammett correlation; DFT
Categories
Funding
- Agenda Estatal de Investigacion (MINECO/AEI/FEDER, UE) [CTQ2016-75960-P]
- Severo Ochoa Excellence Acreditation [SEV-2013-0319]
- Juan de la Cierva postdoctoral fellowship
- European Research Council [321066]
- AGAUR [SGR 818]
- CERCA Program/Generalitat de Catalunya
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We report the alkynylation of C(sp(2))-H bonds with bromoalkynes (inverse-Sonogashira reaction) directed by synthetically useful ester, ketone, and ether groups under rhodium catalysis. Other less common directing groups such as amine, thioether, sulfoxide, sulfone, phenol ester, and carbamate are also suitable directing groups. Mechanistic studies indicate that the reaction proceeds by a turnover limiting C-H activation step via an electrophilic-type substitution.
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