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Synfacts 2023; 19(09): 0883
DOI: 10.1055/s-0042-1752898
Metals in Synthesis

Rhodium Catalyzed Aryl C–H Functionalization with Nitroalkenes

Contributor(s):
Mark Lautens
,
Alexa Torelli
Yang H, Zhang R, Zhang S.-Z, Gu Q, You S.-L. * Shanghai Institute of Organic Chemistry, P. R. of China
Synthesis of Hexamethyl-1,1′-spirobiindane-Based Chiral Spiro Cp Ligands and Their Application in Rhodium-Catalyzed Enantioselective Aryl C–H Addition to Nitroalkenes.

ACS Catal. 2023;
13: 8838-8844
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Key words

rhodium catalysis - C–H functionalization - asymmetric catalysis

Significance

You and co-workers report the use of a spiro cyclopentadienyl rhodium catalyst for the asymmetric C–H functionalization of aryl and heteroaryl amides with nitroalkenes. The reaction was amenable to scale up, and mechanistic studies support that the C−H bond cleavage is reversible and is not involved in the rate-determining step.


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Comment

The authors report a broad substrate scope regarding both coupling partners. Aryl nitro alkenes react with higher enantioselectivity compared to alkyl derivatives. Both heteroaryl and aryl amides, with electron-donating or -withdrawing substituents undergo the transformation with high selectivity.


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Publication History

Article published online:
16 August 2023

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