Issue 43, 2023

Divergent 1,2-carboallylation of terminal alkynes enabled by metallaphotoredox catalysis with switchable triplet energy transfer

Abstract

We report a metallaphotoredox strategy for stereodivergent three-component carboallylation of terminal alkynes with allylic carbonates and alkyl trifluoroborates. This redox-neutral dual catalytic protocol utilizes commercially available organic photocatalyst 4CzIPN and nickel catalysts to trigger a radical addition/alkenyl–allyl coupling sequence, enabling straightforward access to functionalized 1,4-dienes in a highly chemo-, regio-selective, and stereodivergent fashion. This reaction features a broad substrate generality and a tunable triplet energy transfer control with pyrene as a simple triplet energy modulator, offering a facile synthesis of complex trans- and cis-selective skipped dienes with the same set of readily available substrates.

Graphical abstract: Divergent 1,2-carboallylation of terminal alkynes enabled by metallaphotoredox catalysis with switchable triplet energy transfer

Supplementary files

Article information

Article type
Edge Article
Submitted
02 Sep 2023
Accepted
11 Oct 2023
First published
13 Oct 2023
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2023,14, 12143-12151

Divergent 1,2-carboallylation of terminal alkynes enabled by metallaphotoredox catalysis with switchable triplet energy transfer

J. Qin, Z. Zhang, Y. Lu, S. Zhu and L. Chu, Chem. Sci., 2023, 14, 12143 DOI: 10.1039/D3SC04645A

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