- Pd-Catalysed direct C(sp2)-H fluorination of aromatic ketones: Concise access to anacetrapib
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The Pd-cataylsed direct ortho-C(sp2)-H fluorination of aromatic ketones has been developed for the first time. The reaction features good regioselectivity and simple operations, constituting an alternative shortcut to access fluorinated ketones. A concise synthesis of anacetrapib has also been achieved by using late-stage C-H fluorination as a key step.
- Wu, Qiuzi,Mao, Yang-Jie,Zhou, Kun,Wang, Shuang,Chen, Lei,Xu, Zhen-Yuan,Lou, Shao-Jie,Xu, Dan-Qian
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supporting information
p. 4544 - 4547
(2021/05/17)
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Functionalisation in 2 position of benzenes 1,3-disubstituted by para-directing groups has been investigated, involving 2-trimethylsilylated intermediates when the classical methods (particularly these involving the anion in 2 position) are ineffective. Thus 2-trimethylsilyl derivatives of 1,3-dihalo- or 1,3-dimethoxybenzene have been prepared in good yields. Their conversion into the corresponding 1,2,3-trisubstituted benzenes has been conveniently performed upon acetylation, iodination or sulfonation, except in the case of the sulfonation of the 1,3-dimethoxylated compound in which the ipso effect of the silyl group is surpassed by the directing effect of the methoxy substituents. In contrast, whith the same substrate, cyanation in position 2 was successfully carried out using chlorosulfonyl isocyanate: to our knowledge this reaction is the first example of substitution of a trimethylsilyl by a cyano group in the aromatic series.
- Bennetau, Bernard,Rajarison, Florent,Dunogues, Jacques,Babin, Pierre
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p. 10843 - 10854
(2007/10/02)
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- 2-Ethylsulfonyl pyridine 1-oxide derivatives
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Superior herbicidal compounds are provided having the formula: STR1 wherein X and X' are the same or different and are selected from the group consisting of chloro and fluoro.
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