Kanganavaree Chaipot, Kantarod Kritchasorn, Worakul Thanapat, Soorukram Darunee, Kuhakarn Chutima, Chakarawet Khetpakorn, Wattanathana Worawat, Surawatanawong Panida, Reutrakul Vichai, Leowanawat Pawaret
Department of Chemistry, Faculty of Science, Mahidol University, Rama VI Rd, Bangkok 10400, Thailand.
Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand.
J Org Chem. 2024 Oct 18;89(20):15083-15090. doi: 10.1021/acs.joc.4c01747. Epub 2024 Oct 6.
A palladium-catalyzed [3 + 2] annulation of naphthalic anhydrides with internal alkynes has been developed. The present protocol offers an efficient and convenient route to access a series of 1,2-disubstituted acenaphthylenes with excellent functional group compatibility. The reaction is proposed to proceed through a double decarboxylation sequence. The reported synthetic protocols can be extended to napthalene- and perylenedicarboximide-containing substrates. The molecular structures, photophysical properties, and frontier molecular orbitals of the obtained adducts were investigated by X-ray crystallography, UV-vis and fluorescence spectroscopy, and DFT calculations.
已开发出一种钯催化的萘酐与内炔的[3+2]环化反应。本方法提供了一条高效便捷的途径来合成一系列具有优异官能团兼容性的1,2-二取代苊烯。该反应被认为是通过双脱羧序列进行的。所报道的合成方法可扩展到含萘和苝二酰亚胺的底物。通过X射线晶体学、紫外可见光谱和荧光光谱以及密度泛函理论计算对所得加合物的分子结构、光物理性质和前沿分子轨道进行了研究。
