Abstract
The rhodium(I)-catalyzed reaction of alkynes with aryl boronic acids in the presence of formaldehyde results in a CO-gas-free arylative dual-carbonylation to produce γ-butenolide derivatives. The simultaneous loading of phosphine-ligated and phosphine-free rhodium(I) complexes is required for efficient catalysis. The former complex catalyzes the abstraction of a carbonyl moiety from formaldehyde through the activation of its formyl C-H bond (decarbonylation) and the latter catalyzes the subsequent dual-incorporation of the resulting carbonyl unit (carbonylation). The use of larger amounts of the phosphine-ligated rhodium(I) complex generates more carbonyl units, leading to the formation γ-butenolides via the dual-incorporation of the carbonyl unit.
Original language | English |
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Pages (from-to) | 3372-3382 |
Number of pages | 11 |
Journal | Synthesis |
Volume | 53 |
Issue number | 18 |
DOIs | |
State | Published - 2021/04/22 |
Keywords
- C-H activation
- alkynes
- arylboronic acids
- decarbonylation
- formaldehyde
- rhodium
- γ-butenolides
ASJC Scopus subject areas
- Catalysis
- Organic Chemistry