Carbonylative Negishi‐Type Coupling of 2‐Iodoglycals with Alkyl and Aryl Halides

Esteves, Henrique A.; Darbem, Mariana P.; Pimenta, Daniel C.; Stefani, Hélio A.

doi:10.1002/ejoc.201901081

Cited by 21 publications

(6 citation statements)

References 68 publications

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“…Negishi cross-coupling of organozinc reagents with organohalides is a valuable reaction for a raft of applications, including total synthesis . The data gathered in this survey spanned 42 journal articles and 45 individual reactions. ,− The reaction data shows a preference for lower mol % values, particularly from papers published in the past decade. Interestingly, most ppm data points are distributed to lower ppm levels with more than 60% being below 500 ppm.…”

Section: Negishi Cross-couplingmentioning

confidence: 99%

Pd-Catalyzed Cross-Couplings: On the Importance of the Catalyst Quantity Descriptors, mol % and ppm

Horbaczewskyj

Fairlamb

2022

Org. Process Res. Dev.

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This Review examines parts per million (ppm) palladium concentrations in catalytic cross-coupling reactions and their relationship with mole percentage (mol %). Most studies in catalytic cross-coupling chemistry have historically focused on the concentration ratio between (pre)catalyst and the limiting reagent (substrate), expressed as mol %. Several recent papers have outlined the use of “ppm level” palladium as an alternative means of describing catalytic cross-coupling reaction systems. This led us to delve deeper into the literature to assess whether “ppm level” palladium is a practically useful descriptor of catalyst quantities in palladium-catalyzed cross-coupling reactions. Indeed, we conjectured that many reactions could, unknowingly, have employed low “ppm levels” of palladium (pre)catalyst, and generally, what would the spread of ppm palladium look like across a selection of studies reported across the vast array of the cross-coupling chemistry literature. In a few selected examples, we have examined other metal catalyst systems for comparison with palladium.

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Section: Negishi Cross-couplingmentioning

confidence: 99%

Pd-Catalyzed Cross-Couplings: On the Importance of the Catalyst Quantity Descriptors, mol % and ppm

Horbaczewskyj

Fairlamb

2022

Org. Process Res. Dev.

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“…The substrate scope of the reaction was explored and moderate to good yields were observed with olefins bearing electron-neutral and electron-rich groups ( Scheme 48G ). In continuation of their efforts on carbonylation reactions, Helio A. Stefani and co-authors 104 checked the reactivity of unactivated alkyl halides via Negishi type cross-coupling reactions with 2-iodo glycals under Pd catalysis by using carbon monoxide gas as a source of CO ( Scheme 48H ). A library of carbonyl-inserted compounds was generated with a variety of alkyl halides.…”

Section: Pd-catalyzed 2 C -Branched Sugar Synthesismentioning

confidence: 99%

Advances in Pd-catalyzed C–C bond formation in carbohydrates and their applications in the synthesis of natural products and medicinally relevant molecules

Hussain

Hussain²

2021

RSC Adv.

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“…Helio A. Stefaniand co-authors [45] developed a Negishi type cross-coupling reactions of 2-iodo glycals with an unactivated alkyl halides under Pd catalysis by using carbon monoxide gas as a source of CO (Scheme 33). Under this strategy they have successfully prepared a library of carbonyl inserted 2-Cbranched sugars with variety of alkyl halides.…”

Section: Carbonylative Negishi Type Coupling Reactions Of 2-iodoglycalsmentioning

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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Carbonylative Negishi‐Type Coupling of 2‐Iodoglycals with Alkyl and Aryl Halides

Abstract: C-Glycosides are valuable organic compounds in the field of medicinal chemistry due to their ubiquity inside living systems and pronounced biological activity. Herein, we describe an approach to alkyl-ketones bearing glycal units via the Pd- [a]

Cited by 21 publications

References 68 publications

Pd-Catalyzed Cross-Couplings: On the Importance of the Catalyst Quantity Descriptors, mol % and ppm

Pd-Catalyzed Cross-Couplings: On the Importance of the Catalyst Quantity Descriptors, mol % and ppm

Advances in Pd-catalyzed C–C bond formation in carbohydrates and their applications in the synthesis of natural products and medicinally relevant molecules

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

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