Synthesis of 3-Alkenyl Isoquinolines through Redox-Neutral C–H Annulation of Oximes with Alkylacetylenes followed by Dehydrogenation

Although sequential functionalization of multiple C-H bonds is highly attractive to construct complex molecular architectures with no need for substrate prefunctionalization, current reaction patterns are mainly limited to one or more cyclization process(es). Described herein is an unconventional tandem C-H annulation and dehydrogenation of alkylacetylenes, providing facile and modular access to 3-alkenyl isoquinolines with water and valuable dihydrogen as byproducts. This protocol is operationally simple, proceeds well with diverse nonactivated and functionalized alkylacetylenes, and tolerates a wealth of functional groups for streamlined transformations. Combined experimental and computational mechanistic studies unveiled a unique Rh<sup>III</sup>-Rh<sup>I</sup>-Rh<sup>III</sup>-Rh<sup>I</sup>-Rh<sup>III</sup> catalytic cycle involving a sequence of (sp<sup>2</sup>)-H metalation, alkyne insertion, reductive elimination, C(sp<sup>3</sup>)-H metalation, β-H elimination, and oxidative addition.

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Journal
Organic Letters
Published
2025-10-04
DOI
https://doi.org/10.1021/acs.orglett.5c03459
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
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article

Synthesis of 3-Alkenyl Isoquinolines through Redox-Neutral C–H Annulation of Oximes with Alkylacetylenes followed by Dehydrogenation

Zhongyi Zeng, Xuebing Chen, Zhi Zhou, Weihao Li et al.
Organic Letters
Catalytic C–H Functionalization Methods
article

Synthesis of 3-Alkenyl Isoquinolines through Redox-Neutral C–H Annulation of Oximes with Alkylacetylenes followed by Dehydrogenation

Zhongyi Zeng, Xuebing Chen, Zhi Zhou, Weihao Li, Chen Zhou, Minghui Liang, Wei Yi, Yi Wang, Yuanyuan Li, Yang Li, Xuehui Liu, Qingmei Liu, Hui Gao, Wenhong Ouyang, Ying Lin
article en

Abstract

Although sequential functionalization of multiple C-H bonds is highly attractive to construct complex molecular architectures with no need for substrate prefunctionalization, current reaction patterns are mainly limited to one or more cyclization process(es). Described herein is an unconventional tandem C-H annulation and dehydrogenation of alkylacetylenes, providing facile and modular access to 3-alkenyl isoquinolines with water and valuable dihydrogen as byproducts. This protocol is operationally simple, proceeds well with diverse nonactivated and functionalized alkylacetylenes, and tolerates a wealth of functional groups for streamlined transformations. Combined experimental and computational mechanistic studies unveiled a unique Rh<sup>III</sup>-Rh<sup>I</sup>-Rh<sup>III</sup>-Rh<sup>I</sup>-Rh<sup>III</sup> catalytic cycle involving a sequence of (sp<sup>2</sup>)-H metalation, alkyne insertion, reductive elimination, C(sp<sup>3</sup>)-H metalation, β-H elimination, and oxidative addition.

Organic LettersVol. 27(41)
Guangzhou University of Chinese Medicine (CN), Target (United States) (US), Colorado School of Traditional Chinese Medicine (US), Nanfang Hospital (CN), Guangdong Academy of Sciences (CN), State Key Laboratory of Respiratory Disease (CN), Nanfang College Guangzhou, Guangzhou Medical University (CN)
Openalex Percentile: Top 79%
Catalytic C–H Functionalization Methods
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