C(alkyl)–C(vinyl) bond cleavage enabled by Retro-Pallada-Diels-Alder reaction

Qingyang Zhao, Le Yu, Yao-Du Zhang, Yong-Qiang Guo, Ming Chen, Zhi-Hui Ren and Zheng-Hui Guan ()
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Qingyang Zhao: Northwest University
Le Yu: Northwest University
Yao-Du Zhang: Northwest University
Yong-Qiang Guo: Northwest University
Ming Chen: Northwest University
Zhi-Hui Ren: Northwest University
Zheng-Hui Guan: Northwest University

Nature Communications, 2023, vol. 14, issue 1, 1-9

Abstract: Abstract Activation and cleavage of carbon–carbon (C–C) bonds is a fundamental transformation in organic chemistry while inert C–C bonds cleavage remains a long-standing challenge. Retro-Diels-Alder (retro-DA) reaction is a well-known and important tool for C–C bonds cleavage but less been explored in methodology by contrast to other strategies. Herein, we report a selective C(alkyl)–C(vinyl) bond cleavage strategy realized through the transient directing group mediated retro-Diels-Alder reaction of a six-membered palladacycle, which is obtained from an in situ generated hydrazone and palladium hydride species. This unprecedented strategy exhibits good tolerances and thus offers new opportunities for late-stage modifications of complex molecules. DFT calculations revealed that an intriguing retro-Pd(IV)-Diels-Alder process is possibly involved in the catalytic cycle, thus bridging both Retro-Diels-Alder reaction and C–C bond cleavage. We anticipate that this strategy should prove instrumental for potential applications to achieve the modification of functional organic skeletons in synthetic chemistry and other fields involving in molecular editing.

Date: 2023
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DOI: 10.1038/s41467-023-38067-7

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