Aza-[4 + 2]-cycloaddition of benzocyclobutenones into isoquinolinone derivatives enabled by photoinduced regio-specific C–C bond cleavage

Liangkun Yang, Shiyang Li, Lichao Ning, Hansen Zhao, Liang Zhou, Weidi Cao () and Xiaoming Feng ()
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Liangkun Yang: Sichuan University
Shiyang Li: Sichuan University
Lichao Ning: Sichuan University
Hansen Zhao: Sichuan University
Liang Zhou: Sichuan University
Weidi Cao: Sichuan University
Xiaoming Feng: Sichuan University

Nature Communications, 2024, vol. 15, issue 1, 1-9

Abstract: Abstract The activation of C−C bond of benzocyclobutenones under mild reaction conditions remains a challenge. We herein report a photoinduced catalyst-free regio-specific C1−C8 bond cleavage of benzocyclobutenones, enabling the generation of versatile ortho-quinoid ketene methides for aza-[4 + 2]-cycloaddition with imines, which offers a facile route to isoquinolinone derivatives, including seven family members of protoberberine alkaloids, gusanlung A, B, D, 8-oxotetrahydroplamatine, tetrahydrothalifendine, tetrahydropalmatine, and xylopinine. Furthermore, the catalytic enantioselective version of this strategy is also realized by merging synergistic photocatalysis and chiral Lewis acid catalysis. Mechanistic studies provide compelling evidence to rationalize the photoisomerization/cycloaddition cascade process.

Date: 2024
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DOI: 10.1038/s41467-024-55110-3

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