AI Article Synopsis
- The text discusses a discovery in organic chemistry related to the synthesis of benzene derivatives through spontaneous cycloaddition reactions of lighter alkenes and alkynes.
- It highlights the successful formation of diborocarbon compounds, including a neutral 6 π-aromatic diborabenzene and other unique aromatic compounds under ambient conditions without a catalyst.
- DFT calculations indicate that these new compounds possess aromatic characteristics similar to well-known hydrocarbons, showing promise for future research in aromatic chemistry.
Article Abstract
Among the numerous routes organic chemists have developed to synthesize benzene derivatives and heteroaromatic compounds, transition-metal-catalyzed cycloaddition reactions are the most elegant. In contrast, cycloaddition reactions of heavier alkene and alkyne analogues, though limited in scope, proceed uncatalyzed. In this work we present the first spontaneous cycloaddition reactions of lighter alkene and alkyne analogues. Selective addition of unactivated alkynes to boron-boron multiple bonds under ambient conditions yielded diborocarbon equivalents of simple aromatic hydrocarbons, including the first neutral 6 π-aromatic diborabenzene compound, a 2 π-aromatic triplet biradical 1,3-diborete, and a phosphine-stabilized 2 π-homoaromatic 1,3-dihydro-1,3-diborete. DFT calculations suggest that all three compounds are aromatic and show frontier molecular orbitals matching those of the related aromatic hydrocarbons, C6 H6 and C4 H4 (2+) , and homoaromatic C4 H5 (+) .
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| http://dx.doi.org/10.1002/anie.201602384 | DOI Listing |
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