Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 85, Issue 19, Pages 12262-12269Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c01503
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Funding
- Ministerio de Ciencia e Innovacion (MICINN) of Spain [PGC2018-097722-B-I00]
- EU [UNGI08-4E-003]
- Generalitat de Catalunya [2018FI_B 01120]
- Fons Social Europeu [2018FI_B 01120]
- JST [JPMJCR12Z1]
- JSPS [17K19127]
- Grants-in-Aid for Scientific Research [17K19127] Funding Source: KAKEN
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The mechanism for the synthesis of 2,3-bismethylenechromanes obtained by the reaction between silylethynyloxyarenes and allylic pivalates and catalyzed by a palladium complex has been investigated using computational methods rooted in density functional theory. The reaction is promoted by a C-H bond activation and the consequent bond cleavage of both substrates, followed by a novel annulation. The whole mechanism of this reaction is described together with the drawbacks that could block it. The main role played by the allyl rotation, inducing selectivity, together with the lability of the phosphine ligand and base (Cs2CO3) effects are unraveled. Finally, the nature of the substrates was managed, confirming that ortho-allylated silylethynyloxybenzenes lead to the same type of annulated products.
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