Enantioselective Heck/Tsuji−Trost reaction of flexible vinylic halides with 1,3-dienes

Li-Zhi Zhang, Pei-Chao Zhang, Qian Wang, Min Zhou () and Junliang Zhang ()
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Li-Zhi Zhang: Yunnan Minzu University
Pei-Chao Zhang: Second Military Medical University (Naval Medical University)
Qian Wang: Changchun University of Technology
Min Zhou: Yunnan Minzu University
Junliang Zhang: Changchun University of Technology

Nature Communications, 2025, vol. 16, issue 1, 1-7

Abstract: Abstract The enantioselective domino Heck/cross-coupling has emerged as a powerful tool in modern chemical synthesis for decades. Despite significant progress in relative rigid skeleton substrates, the implementation of asymmetric Heck/cross-coupling cascades of highly flexible haloalkene substrates remains a challenging and and long-standing goal. Here we report an efficient asymmetric domino Heck/Tsuji−Trost reaction of highly flexible vinylic halides with 1,3-dienes enabled by palladium catalysis. Specifically, the Heck insertion as stereodetermining step to form ƞ3 allyl palladium complex and in situ trapping with nucleophiles enable efficient Heck/etherification in a formal (4 + 2) cycloaddition manner. Engineering the Sadphos bearing androgynous non-C2-symmetric chiral sulfinamide phosphine ligands are vital component in achieving excellent catalytic reactivity and enantioselectivity. This strategy offers a general, modular and divergent platform for rapidly upgrading feedstock flexible vinylic halides and dienes to various value-added molecules and is expected to inspire the development of other challenging enantioselective domino Heck/cross-couplings.

Date: 2025
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DOI: 10.1038/s41467-025-56142-z

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