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Metal‐Free Temperature‐Controlled Regiodivergent Borylative Cyclizations of Enynes: BCl3‐Promoted Skeletal Rearrangement.
- Source :
-
Angewandte Chemie International Edition . 7/11/2022, Vol. 61 Issue 28, p1-6. 6p. - Publication Year :
- 2022
-
Abstract
- Metal‐free borylative cyclization of biphenyl‐embedded 1,3,5‐trien‐7‐ynes in the presence of simple and inexpensive BCl3 provided synthetically useful borylated building blocks. The outcome of the process depends on the reaction temperature, with borylated phenanthrenes obtained at 60 °C and phenanthrene‐fused borylated cyclobutanes formed at 0 °C. Based on DFT calculations, a mechanism for these novel transformations has been proposed, which involves an uncommon skeletal rearrangement, including migration of a methyl group and alkyne fragmentation, unprecedented in BCl3‐promoted cyclization reactions. [ABSTRACT FROM AUTHOR]
- Subjects :
- *ENYNES
*METHYL groups
*RING formation (Chemistry)
Subjects
Details
- Language :
- English
- ISSN :
- 14337851
- Volume :
- 61
- Issue :
- 28
- Database :
- Academic Search Index
- Journal :
- Angewandte Chemie International Edition
- Publication Type :
- Academic Journal
- Accession number :
- 157800846
- Full Text :
- https://doi.org/10.1002/anie.202205651