Copper-Catalyzed Direct Acyloxylation of C(sp<sup>2</sup>)–H Bonds in Aromatic Amides

Wang, Feifan; Hu, Qiyan; Shu, Chao; Lin, Zhiyang; Min, Dewen; Shi, Tianchao; Zhang, Wu

doi:10.1021/acs.orglett.7b01559

Cited by 48 publications

(23 citation statements)

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“…Previously, Genet and colleagues [22,23] demonstrated that some rhodium complexes could be used to perform 1,4-conjugate addition reaction with MBH adducts. The main advantages of this strategy are its high E-stereoselectivity and the economy of steps, i.e.…”

Section: Resultsmentioning

confidence: 99%

“…We found that the yield was improved when an additive like triphenylphoshine was used in the reaction. [22,23,26] Unfortunately, the reaction between the Morita-Baylis-Hillman adduct 20 and trifluoroboronate salt 24a (see Table 1) furnished 18i in low yield (13 %), after 18 h. We changed catalyst load, temperature and solvents, but we were unable to solve this issue. So, MBH 20 was treated with boronic acid 23 to produce E-cinnamate E-18i, with 72 % yield after 3 hours.…”

Section: Resultsmentioning

confidence: 99%

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A Straightforward Approach to the Synthesis of Disubstituted Cyclopentenones

et al. 2020

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In this paper we describe an approach for the synthesis of a set of new diversely di‐substituted cyclopentenones using Morita–Baylis–Hillman (MBH) adducts as building blocks. The synthesis was performed with few steps, but the overall yield reached 34 %. A key step of this approach is a rhodium mediated 1,4‐addition reaction on adequately functionalised MBH adducts, which leads to the creation of cinnamate ester derivatives with high E selectivity. These intermediates were used as substrates for an intramolecular Friedel‐Crafts cyclisation reaction to achieve the required 2,3‐substituted cyclopentenones. As far as we know, this is the first report to describe the synthesis of substituted cyclopentenones that directly employ MBH adducts as building blocks.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

A Straightforward Approach to the Synthesis of Disubstituted Cyclopentenones

et al. 2020

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“…In 2017, the team of Zhang achieved the ortho ‐C–H direct acyloxylation of the aromatic amides catalyzed by Cu(I) with 8‐aminoquinoline as the directing group (Scheme ) . The highlight of the reaction is that no additives or ligands are needed.…”

Section: Ortho‐c–h Functionalization Of Aromatic Amidesmentioning

confidence: 99%

C–H Functionalization of Aromatic Amides

et al. 2020

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Since the beginning of the 21st century, significant progress has been made in transition metal‐catalyzed C–H functionalization of aromatic amides. The achievements in this field have mainly focused on ortho (proximal) functionalization, there have been far fewer reports on remote C–H functionalization, and para‐ and meta‐selective functionalizations remain a major challenge. Interestingly, there are few related comments in this field. In a few published cases, the scope of the report is relatively narrow, either to comment on the functionalization of a specific directing group or to summarize the functionalization of a specific reaction site. Herein, for the first time, we have comprehensively summarized the C–H functionalization of aromatic amides. This review is divided into three parts: ortho‐, para‐ and meta‐C–H functionalization of aromatic amides, and is subdivided according to the type of catalyst. The directing groups, reaction types, conditions, mechanism and applications of the corresponding reactions are discussed in detail.

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“…[23] Pd-catalyzed chelation-assisted acyloxylation of C-H bonds has also been investigated. [27] Cu II -catalyzed ortho-acyloxylation of the 2-arylpyridines with anhydride using O 2 as the oxidant was reported by Cheng′s group in 2010. [25] Palladium-catalyzed acetoxylation of azoarenes with aryl acylperoxides was described by Zeng et al in 2014 [26] (Scheme 1, Equation 1) Cu Icatalyzed acetoxylation of aryl amids was demonstrated by Zhang and co-workers in 2017.…”

Section: Introductionmentioning

confidence: 99%

“…[25] Palladium-catalyzed acetoxylation of azoarenes with aryl acylperoxides was described by Zeng et al in 2014 [26] (Scheme 1, Equation 1) Cu Icatalyzed acetoxylation of aryl amids was demonstrated by Zhang and co-workers in 2017. [27] Cu II -catalyzed ortho-acyloxylation of the 2-arylpyridines with anhydride using O 2 as the oxidant was reported by Cheng′s group in 2010. [28] Ru II -catlayzed Scheme 1.…”

Section: Introductionmentioning

confidence: 99%