Diverse Synthesis of (Thio)ethers and (Thio)esters Using Halodiborylmethane as a Transformable C1 Building Block
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SCOPUS
- Title
- Diverse Synthesis of (Thio)ethers and (Thio)esters Using Halodiborylmethane as a Transformable C1 Building Block
- Authors
- CHO, SEUNG HWAN; HWANG, CHIWON; JANG, YUNHUI; JUNG, YONGSUK; SEO, JAE YOON; Shin, Kwangmin
- Date Issued
- 2024-08
- Publisher
- American Chemical Society
- Abstract
- The development of effective strategies to forge C-O and C-S bonds in diverse chemical spaces is of considerable interest in synthetic organic chemistry. Herein we report a versatile approach for the modular synthesis of structurally diverse (thio)ethers and (thio)esters via homologative coupling of α-halodiborylmethane followed by transformation of the introduced diborylmethyl group. This method accommodates a wide array of oxygen- and sulfur-containing molecules, including biologically active compounds. The initial coupling exhibits a broad substrate scope, while subsequent diversification of the diborylmethyl moiety enables access to various structural motifs through deborylative alkylation, Zweifel olefination, and boron-Wittig reaction. This protocol efficiently generates diversely functionalized (thio)ethers and (thio)esters, expanding the toolkit for accessing biologically relevant scaffolds. © 2024 American Chemical Society.
- URI
- https://oasis.postech.ac.kr/handle/2014.oak/124224
- DOI
- 10.1021/acs.orglett.4c02510
- ISSN
- 1523-7060
- Article Type
- Article
- Citation
- Organic Letters, vol. 26, no. 33, page. 7010 - 7014, 2024-08
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