Photochemical Synthesis of β‑N-Heterocycle Alcohols via a Coordination-Induced 1,5-Boronate Sigmatropic Rearrangement.

Peng Zou, Dongmin Fu, Jihao Jin, Chenyang Xu, Ruijing Cai, Shi-Jun Li, Yi Zeng, Yu Lan, Yiyun Chen

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Article in JACS Au, 2026. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

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9 authors.

Peng ZouState Key Laboratory of Chemical Biology, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, University of Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.

Dongmin FuCollege of Chemistry, and Pingyuan Laboratory, Zhengzhou University, Zhengzhou, Henan 450001, China.

Jihao JinKey Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, University of Chinese Academy of Sciences, Beijing 100190, China.ORCID https://orcid.org/0009-0003-0921-972X

Chenyang XuState Key Laboratory of Chemical Biology, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, University of Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.

Ruijing CaiState Key Laboratory of Chemical Biology, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, University of Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.

Shi-Jun LiCollege of Chemistry, and Pingyuan Laboratory, Zhengzhou University, Zhengzhou, Henan 450001, China.ORCID https://orcid.org/0000-0001-9872-6245

Yi ZengKey Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, University of Chinese Academy of Sciences, Beijing 100190, China.ORCID https://orcid.org/0000-0003-0694-1795

Yu LanCollege of Chemistry, and Pingyuan Laboratory, Zhengzhou University, Zhengzhou, Henan 450001, China.

Yiyun ChenState Key Laboratory of Chemical Biology, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, University of Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.ORCID https://orcid.org/0000-0003-0916-0994

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

Excited-State Intramolecular Proton Transfer (ESIPT) is an ultrafast nonradiative relaxation pathway that frequently dominates the photophysical fate of conjugated enols, often precluding productive photochemical transformations. Here, we report that bidentate boronate coordination effectively suppresses this process, locking β-N-heterocycle enols into a rigid configuration to enable an efficient photochemical synthesis of β-N-heterocycle alcohols via a 1,5-boronate sigmatropic rearrangement. This strategy circumvents the inherent challenges of hydroxyl acidity and low π-electrophilicity characteristic of the ground-state enol manifold. Operating under mild, metal- and base-free conditions, this protocol facilitates the assembly of 61 diverse aromatic and nonaromatic β-N-heterocycle alcohols (up to 81% yield) using

Indexed as

boronate complexesexcited-state intramolecular proton transferN-heterocyclesphotochemistrysigmatropic rearrangement

Identifiers

PMID42656862

DOI10.1021/jacsau.6c00455

PMCPMC13508102

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