Transition-Metal-Free C–P Bond Formation via Decarboxylative Phosphorylation of Cinnamic Acids with P(O)H Compounds

Liu, Lixin; Zhou, Dan; Dong, Jianyu; Zhou, Yongbo; Yin, Shuang‐Feng; Han, Li‐Biao

doi:10.1021/acs.joc.8b00187

Cited by 43 publications

(15 citation statements)

References 62 publications

(33 reference statements)

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“…39 In 2018, Zhou, Dong, and co-workers achieved metal-free generation of the phosphoryl radical using a KI/tert-butyl perbenzoate (TBPB) catalytic system through a similar radical process (Scheme 14). 40 Unlike the work of Tang, Wang, and co-workers, 38 secondary H-phosphine oxides worked well, but H-phosphinates and H-phosphonates gave low yields under the reaction conditions. This reaction was carried out on a 10mmol scale and was applied to the modification of a bioactive estrone derivative, showing its potential synthetic value in organic synthesis.…”

Section: Short Review Synthesismentioning

confidence: 81%

Phosphorylation of Carboxylic Acids and Their Derivatives with P(O)–H Compounds Forming P(O)–C Bonds

et al. 2020

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Herein, we highlight advances in the phosphorylation of readily available carboxylic acids and their derivatives forming synthetically important P(O)–sp3C, P(O)–sp2C, and P(O)–spC bonds, with an emphasis on the results demonstrated since 2010. This review examines the challenges associated with the use of this strategy for the synthesis of organophosphorus compounds and details advances in the design of catalytic systems that suppress these problems thus resulting in notable progress. Mechanistic details are discussed where available.1 Introduction2 Formation of P(O)–sp3C Bonds3 Formation of P(O)–sp2C Bonds4 Formation of P(O)–spC Bonds5 Outlook and Conclusion

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Section: Short Review Synthesismentioning

confidence: 81%

Phosphorylation of Carboxylic Acids and Their Derivatives with P(O)–H Compounds Forming P(O)–C Bonds

et al. 2020

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“…The acetonitrile solvent has a crucial influence toward the CuSO 4 ⋅ 5H 2 O‐catalyzed reaction, which might due to the formation of acetonitrile‐soluble complex [Cu(MeCN) n ] 2+ intermediate. Radical phosphorylation from H‐phosphonates has become a highly efficient approach to synthesize alkenylphosphine oxide. The phosphorylation could be achieved via the metal‐free, Ni or Cu condition.…”

Section: Radical Additionmentioning

confidence: 99%

“…Radical phosphorylation from H‐phosphonates has become a highly efficient approach to synthesize alkenylphosphine oxide. The phosphorylation could be achieved via the metal‐free, Ni or Cu condition. Conditions are crucial for the selectivity, which may provide inspiration for other radical reactions (Scheme ).…”

Section: Radical Additionmentioning

confidence: 99%

Recent Advances of Cinnamic Acids in Organic Synthesis

et al. 2020

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The great success of cinnamic acids was rooted in their multiple functional groups. Herein, reactions triggered by the radical addition, electrophilic addition, Michael addition and reactions of acids were thoroughly discussed and summarized. Multi-component reactions, rearrange-ments, stereoselective synthesis, coupling, additions will be depicted in detail. This review focused on advances of cinnamic acids in the last decade (2010)(2011)(2012)(2013)(2014)(2015)(2016)(2017)(2018)(2019)(2020). We hope this review will be good for a better understanding of these reagents and future research. * , [7,8] acyl [9] and ketonic [10] radicals were reported. Toluene, [8a-c,9] boron reagents, [8d] aldehydes, [8e] acids, [9b,c] amides, [9d,12e-f] ketones, [10a-b] ethers, [11a-c] alcohols, [12a] epoxides, [12b] nitriles [12a] were able to function as radical precursors.Mao and co-workers [4] reported the decarboxylative methylation of cinnamic acids. The DTBP was employed not only as the oxidant, but also as the methyl source.C vinyl À CF 3 compounds (like Panomifene, and Cyhalothrin) were useful in medicinal chemistry. [5b] Hence, numerous efforts have been devoted to the preparation of these compounds. In this decade, several applications of air-stable Togni's reagent [5a-c,6a] or NaSO 2 CF 3 [5d-f,6b] for the direct C vinyl À CF 3 construction from cinnamic acids have been reported. These radical addition and decarboxylative methods usually required a metal-catalyst (Ir, [5a] Cu [5c,e,6b] ) (Scheme 3)Hu and co-workers [6a] presented a protocol for the construction of C sp2 À CF 2 SO 2 R bonds with a Togni-type reagent. The [a] L.Scheme 1. Classification by mechanism Scheme 2. Radical cascade.

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“…A curious room temperature decarboxylative formation of alkenyl phosphine oxides has been has been achieved through reaction of diphenylphosphine oxide and cinnamic acids in the presence of TBPB and catalytic iodide (Figure ) . Activation of the perester by iodide is likely to lead to iodine and tert ‐butoxyl radical; the authors propose that HAT from the phosphine oxide generates a P‐centered radical that undergoes addition to the alkene.…”

Section: Reactionsmentioning

confidence: 99%