Monodentate transient directing group promoted Pd-catalyzed direct ortho-C‒H arylation and chlorination of α-ketoesters for three-step synthesis of Cloidogrel racemate

Wang, Jian; Wu, Yongdi; Xu, Wengang; Lü, Xiaohong; Wang, Yunfang; Liu, Guangyuan; Sun, Bing; Zhou, Yirong; Zhang, Fanglin

doi:10.1016/j.tet.2022.132980

Cited by 2 publications

(2 citation statements)

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“…They first developed a palladium-catalyzed chlorination reaction and applied it to the synthesis of clopidogrel (Scheme 19.a). [37] On this class of substrates, an arylation reaction was described and, in function of the reaction time (24 h or 48 h), ortho-arylated products 65 (Scheme 19.b) or cyclized 9-fluorenols 67 (Scheme 19.c) were isolated. [37,38] Very recently, the same group achieved an iridium-catalyzed amidation reaction with sulfonyl azides as nitrogen source (Scheme 19.d).…”

Section: 1b Ketonesmentioning

confidence: 99%

“…[37] On this class of substrates, an arylation reaction was described and, in function of the reaction time (24 h or 48 h), ortho-arylated products 65 (Scheme 19.b) or cyclized 9-fluorenols 67 (Scheme 19.c) were isolated. [37,38] Very recently, the same group achieved an iridium-catalyzed amidation reaction with sulfonyl azides as nitrogen source (Scheme 19.d). [39] The synthesized amido-esters 69 could be converted in one step into complex heterocycles such as isatin 70 or 1,2-dihydroquinoline 71.…”

Section: 1b Ketonesmentioning

confidence: 99%

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C−H Functionalization of Aldehydes and Ketones with Transient Directing Groups: Recent Developments

2023

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In order to directly functionalize C−H bonds of complex molecules and, in particular, to control the regioselectivity of the reaction, a wide range of directing groups has been used. However, these directing groups need to be installed and removed for further applications, which may limit the use of C−H activation in synthesis. Concerning aldehydes and ketones, a transient directing group strategy has recently emerged to overcome this drawback. The addition of an additive, in general an amine, allowed the in situ formation of the real directing group to achieve C−H activation. This review presents the latest developments in the field over the period 2020–2023.

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Section: 1b Ketonesmentioning

confidence: 99%

Section: 1b Ketonesmentioning

confidence: 99%

C−H Functionalization of Aldehydes and Ketones with Transient Directing Groups: Recent Developments

2023

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Iridium-Catalyzed Direct Ortho-C–H Amidation of α-Ketoesters with Sulfonyl Azides Using a Transient Directing Group Strategy

Sun

Lü

et al. 2023

J. Org. Chem.

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Direct C−H amidation of α-ketoesters was accomplished using various organic azides as the amino source through the combination of transient directing group strategy and iridium catalysis. Excellent functional group tolerance and wide substrate scope were explored under simple and mild conditions. Importantly, it was found that the steric hindrance of the ester moiety played a pivotal role for the reaction efficacy. In addition, the reaction could be enlarged to gram scale, and several useful heterocycles were readily constructed via one-step late-stage derivatization.

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Monodentate transient directing group promoted Pd-catalyzed direct ortho-C‒H arylation and chlorination of α-ketoesters for three-step synthesis of Cloidogrel racemate

Cited by 2 publications

References 43 publications

C−H Functionalization of Aldehydes and Ketones with Transient Directing Groups: Recent Developments

C−H Functionalization of Aldehydes and Ketones with Transient Directing Groups: Recent Developments

Iridium-Catalyzed Direct Ortho-C–H Amidation of α-Ketoesters with Sulfonyl Azides Using a Transient Directing Group Strategy

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