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Direct amidation of metallaaromatics: access to N-functionalized osmapentalynes via a 1,5-bromoamidated intermediate† † Electronic supplementary information (ESI) available: Characterization details of new compounds, crystallographic details, NMR spectra. CCDC 2053993 (S), 2054261 (1), 2054330 (2a), 2054286 (2b), 2054272 (2c), 2054274 (2d), 2054285 (2e), 2054269 (4a) and 2069503 (5). For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/d1sc01571k

ABSTRACT: The direct C–H amidation or imidation of metallaaromatics with N-bromoamides or imides has been achieved under mild conditions and leads to the formation of a family of N-functionalized metallapentalyne derivatives. A unique 1,5-bromoamidated species has been identified, and can be viewed as a σH-adduct intermediate in a nucleophilic aromatic substitution. The 1,5-addition of both electrophilic and nucleophilic moieties into the metallaaromatic framework demonstrates a novel pathway in contrast to the typical radical process of arene C–H amidation involving N-haloamide reagents. The direct C–H amidation of metallapentalyne has been achieved under mild conditions in which key 1,5-bromoamidated intermediates was determined.

SUBMITTER: Wang H

PROVIDER: S-EPMC8115065 | biostudies-literature |

REPOSITORIES: biostudies-literature

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