期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 59, 期 10, 页码 3917-3921出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201914875
关键词
[1; 1; 1]propellane; bicyclo[1; 1; 1]pentanes; borylation; multicomponent reactions; Zweifel olefination
资金
- EPSRC [EP/S017801/1]
- EU [792439]
- EPSRC [EP/S017801/1] Funding Source: UKRI
- Marie Curie Actions (MSCA) [792439] Funding Source: Marie Curie Actions (MSCA)
1,3-Disubstituted bicyclo[1.1.1]pentanes (BCPs) are valuable bioisosteres of para-substituted aromatic rings. The most direct route to these structures is via multicomponent ring-opening reactions of [1.1.1]propellane. However, challenges associated with these transformations mean that difunctionalized BCPs are more commonly prepared by multistep reaction sequences with BCP-halide intermediates. Herein, we report three- and four-component 1,3-difunctionalizations of [1.1.1]propellane with organometallic reagents, organoboronic esters, and a variety of electrophiles. This process is achieved by trapping intermediate BCP-metal species with boronic esters to form boronate complexes, which are versatile intermediates whose electrophile-induced 1,2-metallate rearrangement chemistry enables a broad range of C-C bond-forming reactions.
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