Citation: Yifan Wang, Yuanyuan Ping, Wangqing Kong. Synergistic Pd/Cu-catalyzed regio- and stereoselective cascade Heck cyclization/borylation/cross-coupling[J]. Chinese Chemical Letters, ;2023, 34(12): 108453. doi: 10.1016/j.cclet.2023.108453 shu

Synergistic Pd/Cu-catalyzed regio- and stereoselective cascade Heck cyclization/borylation/cross-coupling

The Institute for Advanced Studies (IAS), Wuhan University, Wuhan 430072, China

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00033369@whu.edu.cn

wqkong@whu.edu.cn

Received Date: 13 January 2023
Revised Date: 4 April 2023
Accepted Date: 12 April 2023
Available Online: 14 April 2023

Figures(7)

A cooperative Pd/Cu-catalyzed three-component cross-coupling reaction of alkynes, B₂Pin₂ and alkene-tethered aryl halides is reported. This reaction proceeds under mild conditions and shows broad substrate scope, providing a variety of heterocycles containing tetrasubstituted alkenylboronate moieties in synthetically useful yields with excellent chemoselectivity and regioselectivity. This transformation features the catalytic generation of β-borylalkenylcopper intermediates and their use in Pd-catalyzed Heck cyclization/cross-couplings. An enantioselective cascade cyclization/cross-coupling process has also been developed for the synthesis of enantiomerically enriched oxindole bearing a tetrasubstituted alkenylboronate moiety.
- Palladium/copper catalysis,
- Heck cyclization,
- Alkene difunctionalization,
- Cross-coupling,
- Borylation
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