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Synthesis 2023; 55(11): 1744-1751
DOI: 10.1055/a-1970-4584
DOI: 10.1055/a-1970-4584
paper
Special Issue dedicated to Prof. Cristina Nevado, recipient of the 2021 Dr. Margaret Faul Women in Chemistry Award
Borylation of Alkenyl Carbamates by Means of Sodium Metal
This work was supported by Japan Science and Technology Agency (JST) CREST Grant Number JPMJCR19R4 as well as Japan Society for the Promotion of Science (JSPS) KAKENHI Grant Number JP19H00895. F.T. acknowledges Japan Society for the Promotion of Science Predoctoral Fellowship KAKENHI Grant Number JP20J22814. H.S. thanks The Kyoto University Foundation for financial support. H.Y. thanks The Asahi Glass Foundation for financial support.
Abstract
Treatment of alkenyl carbamates with sodium dispersion and a co-existing boron electrophile affords alkenylboronates via the reductive cleavage of the vinylic C–O bond. The key to this borylation is an instant trapping of reactive organosodium species with the co-existing boron electrophile.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1970-4584.
- Supporting Information
Publication History
Received: 13 September 2022
Accepted after revision: 31 October 2022
Accepted Manuscript online:
31 October 2022
Article published online:
29 November 2022
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Selected reviews on transformations of C–O bonds including reactions of carbamates:
Selected examples of reductive transformations using sodium dispersion reported by other groups:
Selected recent reviews on the OCF3 group: