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Direct photo-induced reductive Heck cyclization of indoles for the efficient preparation of polycyclic indolinyl compounds.


ABSTRACT: The photo-induced cleavage of C(sp2)-Cl bonds is an appealing synthetic tool in organic synthesis, but usually requires the use of high UV light, photocatalysts and/or photosensitizers. Herein is described a direct photo-induced chloroarene activation with UVA/blue LEDs that can be used in the reductive Heck cyclization of indoles and without the use of a photocatalyst or photosensitizer. The indole compounds examined display room-temperature phosphorescence. The photochemical reaction tolerates a panel of functional groups including esters, alcohols, amides, cyano and alkenes (27 examples, 50-88% yields), and can be used to prepare polycyclic compounds and perform the functionalization of natural product analogues in moderate to good yields. Mechanistic experiments, including time-resolved absorption spectroscopy, are supportive of photo-induced electron transfer between the indole substrate and DIPEA, with the formation of radical intermediates in the photo-induced dearomatization reaction.

SUBMITTER: Yu D 

PROVIDER: S-EPMC8565399 | biostudies-literature | 2021 Nov

REPOSITORIES: biostudies-literature

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Direct photo-induced reductive Heck cyclization of indoles for the efficient preparation of polycyclic indolinyl compounds.

Yu Daohong D   To Wai-Pong WP   Liu Yungen Y   Wu Liang-Liang LL   You Tingjie T   Ling Jesse J   Che Chi-Ming CM  

Chemical science 20210916 42


The photo-induced cleavage of C(sp<sup>2</sup>)-Cl bonds is an appealing synthetic tool in organic synthesis, but usually requires the use of high UV light, photocatalysts and/or photosensitizers. Herein is described a direct photo-induced chloroarene activation with UVA/blue LEDs that can be used in the reductive Heck cyclization of indoles and without the use of a photocatalyst or photosensitizer. The indole compounds examined display room-temperature phosphorescence. The photochemical reactio  ...[more]

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