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Synthesis 2021; 53(17): 3065-3074
DOI: 10.1055/a-1328-6436
DOI: 10.1055/a-1328-6436
special topic
Bond Activation – in Honor of Prof. Shinji Murai
Dienylation of Unfunctionalized Arenes with 1,6-Diynes via Rhodium-Catalyzed Directing-Group-Free C–H Bond Activation
This work was supported partly by a Grant-in-Aid for Scientific Research (No. JP19H00893 to K.T. and No. JP20K22521 to Y.N.) from the Japan Society for the Promotion of Science (JSPS, Japan).
Abstract
It has been established that the dienylation of unfunctionalized arenes with 1,6-diynes, possessing aryl groups at the diyne termini, proceeds to give the corresponding dienylated arenes in the presence of a catalytic amount of an electron-deficient cyclopentadienyl rhodium(III) complex, [CpERhCl2]2, and a stoichiometric amount of silver carbonate. Experimental and theoretical mechanistic studies revealed that a CpERh(I) complex generated in situ might catalyze the present dienylation reaction.
Key words
alkynes - dienylation - directing group-free C–H bond activation - rhodium - unfunctionalized arenesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1328-6436.
- Supporting Information
Publication History
Received: 13 November 2020
Accepted after revision: 03 December 2020
Accepted Manuscript online:
03 December 2020
Article published online:
11 January 2021
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For selected recent reviews, see:
For the reactions of aryketones with 1,6-enynes, see:
For selected recent examples of the transition-metal-catalyzed and non-directed sp2 C–H bond olefination of unfunctionalized arenes, see:
For applications of 1 in C–H bond functionalizations other than annulation reactions, see:
For examples of the CpRh(III) complex-catalyzed C–H bond functionalization, see:
The RhCl3/i-Pr2NEt catalyzed [2+2+2] cycloaddition of alkynes, in which RhCl3 would be reduced by i-Pr2NEt to afford a rhodium(I) complex, was reported, see: