Direct Synthesis of 1,3-Dien-2-yl Esters from α-Allenols and Carboranyl Carboxylic Acids
-carboxylated carboranes with α-allenols, enabling direct access to carborane-containing 1,3-dien-2-yl esters under mild conditions. This operationally simple protocol proceeds via dehydration of a protonated α-allenol to generate a putative α-allenyl carbocation, which is efficiently intercepted by the corresponding carboranyl carboxylate. The synthetic utility of the resulting dienyl esters is demonstrated through Diels-Alder reactions with representative dienophiles. Mechanistic investigations support the unique reactivity of carboranyl carboxylic acids and a pathway distinct from transition-metal-catalyzed intramolecular acyloxy migration manifolds.
Authors
- Phil Ho Lee (ORCID: https://orcid.org/0000-0001-8377-1107)
- Tae Hyeon Kim (ORCID: https://orcid.org/0000-0001-9528-0006)
- Euijae Lee (ORCID: https://orcid.org/0000-0002-8735-5474)
- Koustav Pal
Institutions
- Kangwon National University (KR)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2026-05-17
- DOI
- https://doi.org/10.1021/acs.joc.6c00340
- Primary Topic
- Boron Compounds in Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- National Research Foundation of Korea