Natural Product Synthesis via Palladium-Catalyzed Carbonylation

Bai, Yu; Davis, Dexter C.; Dai, Mingji

doi:10.1021/acs.joc.7b00009

Cited by 150 publications

(52 citation statements)

References 119 publications

(64 reference statements)

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“…[9][10][11][12][13] From the point view of diversity,t he transition-metal-catalyzed arylcarbonylative coupling of internal alkynes with aryl halidesa nd organometallic compounds should provide an efficient and direct method for the synthesis of tetrasubstituted enones and relatedc ompounds. [9][10][11][12][13] From the point view of diversity,t he transition-metal-catalyzed arylcarbonylative coupling of internal alkynes with aryl halidesa nd organometallic compounds should provide an efficient and direct method for the synthesis of tetrasubstituted enones and relatedc ompounds.…”

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confidence: 99%

“…Amongt he various transition-metal-catalyzedt ransformations, the carbonylative reaction is an efficient methodf or incorporating C1 synthons into organic compounds to give various carbonyl-containing compounds. [9][10][11][12][13] From the point view of diversity,t he transition-metal-catalyzed arylcarbonylative coupling of internal alkynes with aryl halidesa nd organometallic compounds should provide an efficient and direct method for the synthesis of tetrasubstituted enones and relatedc ompounds. Surprisingly, although the synthesis of tetrasubstituted olefins by the transition-metal-catalyzed carbometalation of alkynes has been widely studied, [14][15] the carbonylative version has been scarcely reported and proven to be ac hallenge.…”

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confidence: 99%

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Palladium‐Catalyzed Tunable Carbonylative Synthesis of Enones and Benzofulvenes

Peng

Spannenberg

et al. 2019

Chemistry A European J

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Ap alladium-catalyzed four-component carbonylative coupling reaction involving aryl halides, internal alkynes, arylboronic acids, and CO has been developedf or the first time.A ll-carbon substituted a-unsaturated ketones and benzofulvenes can be selectively obtained in a highly regio-and stereocontrolled manner.U sing Cu(TFA) 2 as the additive, as eries of tetrasubstituted a-unsaturated ketonesw ere prepared in moderate to high yields. Using more acidic Lewis acid Cu(OTf) 2 as the additive, multisubstitutedb enzofluvenes were synthesized in moderate yields. This efficient methodology involved the formation of three new CÀCb onds, and provided ad ivergent methodf or the quick construction of multisubstituted aunsaturated ketones and benzofulvenes from easily available starting materials.Scheme1.Carbonylative synthesis of tetrasubstituted enones.[a] Dr.Supporting information and the ORCID identification number(s) for the author(s) of this articlecan be found under: https://doi.

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confidence: 99%

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Palladium‐Catalyzed Tunable Carbonylative Synthesis of Enones and Benzofulvenes

Peng

Spannenberg

et al. 2019

Chemistry A European J

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“…[34] CO can act as an excellent ligand for Pd having a strong affinity towards both Pd(0) and Pd(II) since it can act as σdonor as well as π-acceptor. [35] The importance of palladiumcatalysed carbonylation chemistry is well exemplified in alkoxycarbonylation; [36] aminocarbonylation; [37] carbonylative Heck; [38] carbonylative Suzuki-Miyaura; [39] carbonylative Sonogashira reactions; [40] and so forth (Figure 3). In this review, we have only focussed on the carbonylation reaction of 2-halo glycals with various coupling partners for the synthesis of 2-C-branched glycoconjugates.…”

Section: Carbonylation Reactions Of 2-halo Glycals and Their Applicatmentioning

confidence: 99%

2‐Halo Glycals as “Synthon” for 2‐C‐Branched Sugar: Recent Advances and Applications in Organic Synthesis

2020

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Glycals are unsaturated sugars having an enolic double bond present inside the ring and act as a versatile synthon for the synthesis of natural products and biologically important molecules. The lone pair of endocyclic ring oxygen which is in conjugation with the enolic double bond alters the reactivity of both unsaturated carbons of glycals and directs the selectivity of the incoming group at a particular center. Since the enolic double bond is very much prone to undergo various types of reactions such as epoxidation, addition, formylation, nitration halogenation, etc.; and such type of activated glycals or the derivatives of glycal have been extensively utilized as a precursor for the synthesis of branched sugars. 2-haloglycals have emerged as an important building block for the functionalization at C-2 position of glycals via metal-catalyzed cross-coupling reactions such as Heck, Suzuki, Sonogashira and carbonylative cross-coupling reactions. In this review, we have summarized the recent progress on the utilization of 2-haloglycals for the synthesis of 2-C-branched sugars and further transformation of branched sugars into annulated sugars, heterocycles, and glycoconjugates.[a] Dr.

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“…[4][5][6][7] The former method involves a strongly basic metalated intermediate that is incompatible with sensitive functional groups, while the latter proceeds smoothly under weakly basic conditions.…”

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confidence: 99%