- Aromatic C-H Methylation and Other Functionalizations via the Rh(III)-Catalyzed Migratory Insertion of Bis(phenylsulfonyl)carbene and Subsequent Transformations
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The Rh(III)-catalyzed migratory insertion of bis(phenylsulfonyl)carbene into aromatic C-H bonds has been developed. A variety of bis(phenylsulfonyl)methyl derivatives were prepared with good yields under mild conditions. The methylated products were readily obtained after reductive desulfonylation. Furthermore, the diverse transformations of bis(phenylsulfonyl)methyl to trideuteriomethyl, aldehyde, and other functional groups were demonstrated.
- Chen, Lei,Peng, Rui-Jun,Zhang, Xue-Jing,Yan, Ming,Chan, Albert S. C.
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p. 10177 - 10189
(2021/07/28)
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- Cobalt-catalysed C–H methylation for late-stage drug diversification
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The magic methyl effect is well acknowledged in medicinal chemistry, but despite its significance, accessing such analogues via derivatization at a late stage remains a pivotal challenge. In an effort to mitigate this major limitation, we here present a strategy for the cobalt-catalysed late-stage C–H methylation of structurally complex drug molecules. Enabling broad applicability, the transformation relies on a boron-based methyl source and takes advantage of inherently present functional groups to guide the C–H activation. The relative reactivity observed for distinct classes of functionalities were determined and the sensitivity of the transformation towards a panel of common functional motifs was tested under various reaction conditions. Without the need for prefunctionalization or postdeprotection, a diverse array of marketed drug molecules and natural products could be methylated in a predictable manner. Subsequent physicochemical and biological testing confirmed the magnitude with which this seemingly minor structural change can affect important drug properties. [Figure not available: see fulltext.]
- Ackermann, Lutz,Friis, Stig D.,Johansson, Magnus J.
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p. 511 - 519
(2020/06/05)
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- Rhodium(III)-Catalyzed ortho -C-H Alkylation of 2-Arylbenzothiazoles and 2-Arylthiazoles with Potassium Alkyltrifluoroborates
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A general and efficient Rh(III)-catalyzed ortho-C-H alkylation of 2-arylbenzothizazoles and 2-arylthiazoles with potassium alkyltrifluoroborates has been developed. The present method leads to the construction of a library of alkylated 2-arylbenzothiazole
- Ping, Yuanyuan,Chen, Zhaobin,Ding, Qiuping,Peng, Yiyuan
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p. 2015 - 2024
(2017/04/26)
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- Programmed synthesis of arylthiazoles through sequential C-H couplings
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A programmed synthesis of privileged arylthiazoles via sequential C-H couplings catalyzed by palladium or nickel catalysts has been accomplished. This versatile protocol can supply all possible arylthiazole substitution patterns (2-aryl, 4-aryl, 5-aryl, 2
- Tani, Satoshi,Uehara, Takahiro N.,Yamaguchi, Junichiro,Itami, Kenichiro
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p. 123 - 135
(2014/01/06)
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- Efficient coupling of heteroaryl halides with arylboronic acids in the presence of a palladium-tetraphosphine catalyst
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Cis, cis, cis-1,2,3,4-tetrakis(diphenylphosphinomethyl) cyclopentane: ·1/2[PdCl(C3H5)]2 system catalyses the Suzuki cross-coupling of heteroaryl halides with a range of arylboronic acids with very high ratio substrate/catalyst in good yields. Substrates such as pyridines, quinolines, thiophenes, an indole, pyrimidines or a furane have been used successfully.
- Feuerstein, Marie,Doucet, Henri,Santelli, Maurice
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p. 327 - 336
(2007/10/03)
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