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Synthesis 2024; 56(13): 1989-1998
DOI: 10.1055/a-2323-0633
DOI: 10.1055/a-2323-0633
feature
Remote-Carbonyl-Directed Consecutive Arylation of Terminal Alkenes for the Synthesis of Tetrasubstituted Olefins
This work was supported by the National Key Research and Development Program of China (2018YFA0704502), the National Natural Science Foundation of China (grant nos. 21871261, 21931011) and the Fujian Science and Technology Innovation Laboratory for Optoelectronic Information of China (2021ZZ105).
Abstract
The highly efficient synthesis of all-carbon tetrasubstituted olefins has been a challenge for decades, especially of multi-aryl-substituted olefins which are widely used in functional organic materials and pharmaceuticals. This work presents a carbonyl-directed palladium-catalyzed consecutive arylation of terminal alkenes with aryl iodides under mild conditions, in which a series of triarylated tetrasubstituted olefins were obtained in moderate yields. Because a weak chelation effect is generally difficult to support such a thorough trifold Heck arylation, and β-trans-selective alkenyl C–H activation cannot be achieved via a twisted endo-metallocyclic intermediate, the key to success is the compatibility between several mechanisms, including Heck reaction, C–H activation and E/Z-isomerization. Here, the judicious selection of a flexible-alkyl-chain-tethered carbonyl group seems to be critical, as it provides a proper chelation effect that not only assists distal alkenyl functionalization or isomerization, but also avoids byproducts caused by other possible β-H elimination or migration. The strategy developed herein greatly streamlines the preparation of the target molecules, and the protocol covers a range of readily available terminal alkenes bearing a native directing group (i.e., aldehyde, ketone and ester) and aryl iodides.
Key words
carbonyl-directed - consecutive arylation - E/Z-isomerization - all-carbon tetrasubstituted olefins - alkenyl C–H activation - Mizoroki–Heck reactionSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2323-0633.
- Supporting Information
Publication History
Received: 15 April 2024
Accepted after revision: 10 May 2024
Accepted Manuscript online:
10 May 2024
Article published online:
23 May 2024
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Some recent examples of all-carbon tetrasubstituted olefin synthesis via alkynyl or propadienyl carbometalation:
Some reviews on chelation-assisted Mizoroki–Heck reactions:
Some recent examples of chelation-assisted Mizoroki–Heck reactions:
Chelation-assisted all-carbon tetrasubstituted olefin synthesis via Heck arylation:
Some reviews on chelation-assisted alkenyl C–H functionalization:
Some recent examples of geminal group directed alkenyl C–H functionalization:
Some recent examples of vicinal group directed alkenyl C–H functionalization:
Some examples of the synthesis of all-carbon tetrasubstituted olefins via chelation-assisted alkenyl C–H activation: