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Synfacts 2015; 11(8): 0823
DOI: 10.1055/s-0034-1378778
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Rhodium-Catalyzed Asymmetric Arylation of Diarylmethylamines

Contributor(s):
Mark Lautens
,
Zafar Qureshi
,
Hyung Yoon
Huang Y, Hayashi T * National University of Singapore, Singapore
Asymmetric Synthesis of Triarylmethanes by Rhodium-Catalyzed Enantioselective Arylation of Diarylmethylamines with Arylboroxines.

J. Am. Chem. Soc. 2015;
137: 7556-7559
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Further Information

Publication History

Publication Date:
20 July 2015 (online)

 
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Key words

rhodium - diarylmethylamines - arylation

Significance

Triarylmethanes are an important class of compounds that are useful in medicinal chemistry and materials science. Reports on their asymmetric synthesis include cross-coupling (B. L. H. Taylor et al. Angew. Chem. Int. Ed. 2013, 51, 7790), selective oxidation (B. F. Shi et al. Angew. Chem. Int. Ed. 2008, 47, 4882) and Friedel–Crafts reaction (M.-H. Zhuo et al. Org. Lett. 2014, 16, 1096). The authors report a rhodium-catalyzed 1,4-addition strategy of an o-quinone methide generated in situ for the synthesis of chiral triarylmethanes.


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Comment

A variety of triarylmethanes were generated using this strategy. Substitution of all three aryl groups were tolerated well, giving good to excellent enantioselectivities. One limitation was noted: the enantioselectivity was reduced for substrates with ortho-substitution on Ar1. The final products could also be deoxygenated through triflation followed by palladium-catalyzed hydrogenolysis.


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