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

被引：4
作者：
Yang, Liangkun [1 ]
Li, Shiyang [1 ]
Ning, Lichao [1 ]
Zhao, Hansen [1 ]
Zhou, Liang [1 ]
Cao, Weidi [1 ]
Feng, Xiaoming [1 ]
机构：
[1] Sichuan Univ, Coll Chem, Key Lab Green Chem & Technol, Minist Educ, Chengdu 610064, Peoples R China
来源：
NATURE COMMUNICATIONS | 2024年 / 15卷 / 01期
基金：
中国国家自然科学基金;
关键词：
RH-CATALYZED CARBOACYLATION; NITROGEN-HETEROCYCLES; PHOTOCHEMISTRY; ACTIVATION; OLEFINS; GENERATION; INSERTION; RHODIUM; CHEMO; REGIOSELECTIVITIES;
D O I：
10.1038/s41467-024-55110-3
中图分类号：
O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];
学科分类号：
07 ; 0710 ; 09 ;
摘要：
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.
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页数：9
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