Palladium‐Catalyzed Fluorosulfonylvinylation of Organic Iodides

Zha, Gao‐Feng; Zheng, Qinheng; Leng, Jing; Wu, Peng; Qin, Hua‐Li; Sharpless, K. Barry

doi:10.1002/anie.201701162

Cited by 110 publications

(56 citation statements)

References 22 publications

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“…The products 52 proved to be selectively addressable bis-electrophiles for sulfur(VI) fluoride exchange (SuFEx) click chemistry, in which either the alkenyl moiety or the sulfonyl fluoride group could be exclusively attacked by nucleophiles under defined conditions, making these simple cores attractive for covalent drug discovery [60]. Later, Qin and Sharpless employed a similar strategy for the synthesis of 2-(hetero)arylethenesulfonylfluorides (54) and 1,3-dienylsulfonyl fluorides (56) (Scheme 9) [61]. They found that a combination of catalytic Pd(OAc)2 with a stoichiometric amount of silver(I) trifluoroacetate enabled the coupling process between either an (hetero)aryl or alkenyl iodide (53 or 55) and ethenesulfonyl fluoride (ESF, 51).…”

Section: Fluorine-containing Vinyl Sulfur Compounds As the Cross-coupmentioning

confidence: 99%

“…They found that a combination of catalytic Pd(OAc)2 with a stoichiometric amount of silver(I) trifluoroacetate enabled the coupling process between either an (hetero)aryl or alkenyl iodide (53 or 55) and ethenesulfonyl fluoride (ESF, 51). The reaction was demonstrated in the successful synthesis Later, Qin and Sharpless employed a similar strategy for the synthesis of 2-(hetero)arylethenesulfonylfluorides (54) and 1,3-dienylsulfonyl fluorides (56) (Scheme 9) [61]. They found that a combination of catalytic Pd(OAc) 2 with a stoichiometric amount of silver(I) trifluoroacetate enabled the coupling process between either an (hetero)aryl or alkenyl iodide (53 or 55) and ethenesulfonyl fluoride (ESF, 51).…”

Section: Fluorine-containing Vinyl Sulfur Compounds As the Cross-coupmentioning

confidence: 99%

“…They found that a combination of catalytic Pd(OAc) 2 with a stoichiometric amount of silver(I) trifluoroacetate enabled the coupling process between either an (hetero)aryl or alkenyl iodide (53 or 55) and ethenesulfonyl fluoride (ESF, 51). The reaction was demonstrated in the successful synthesis of eighty-eight compounds in up to 99% yields, including the unprecedented 2-heteroarylethenesulfonyl fluorides and 1,3-dienylsulfonyl fluorides [61]. These substituted ethenesulfonyl fluorides are useful building blocks for consequent synthetic transformations [61].…”

Section: Fluorine-containing Vinyl Sulfur Compounds As the Cross-coupmentioning

confidence: 99%

“…The reaction was demonstrated in the successful synthesis of eighty-eight compounds in up to 99% yields, including the unprecedented 2-heteroarylethenesulfonyl fluorides and 1,3-dienylsulfonyl fluorides [61]. These substituted ethenesulfonyl fluorides are useful building blocks for consequent synthetic transformations [61]. of eighty-eight compounds in up to 99% yields, including the unprecedented 2-heteroarylethenesulfonyl fluorides and 1,3-dienylsulfonyl fluorides [61].…”

Section: Fluorine-containing Vinyl Sulfur Compounds As the Cross-coupmentioning

confidence: 99%

“…of eighty-eight compounds in up to 99% yields, including the unprecedented 2-heteroarylethenesulfonyl fluorides and 1,3-dienylsulfonyl fluorides [61]. These substituted ethenesulfonyl fluorides are useful building blocks for consequent synthetic transformations [61].…”

Section: Fluorine-containing Vinyl Sulfur Compounds As the Cross-coupmentioning

confidence: 99%

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Pd-Catalyzed Mizoroki-Heck Reactions Using Fluorine-Containing Agents as the Cross-Coupling Partners

Yang

Zhao

et al. 2018

Catalysts

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Abstract:The Mizoroki-Heck reaction represents one of the most convenient methods for carbon-carbon double bond formation in the synthesis of small organic molecules, natural products, pharmaceuticals, agrochemicals, and functional materials. Fluorine-containing organic compounds have found wide applications in the research areas of materials and life sciences over the past several decades. The incorporation of fluorine-containing segments into the target molecules by the Mizoroki-Heck reactions is highly attractive, as these reactions efficiently construct carbon-carbon double bonds bearing fluorinated functional groups by simple procedures. This review summarizes the palladium-catalyzed Mizoroki-Heck reactions using various fluorine-containing reagents as the cross-coupling partners. The first part of the review describes the Pd-catalyzed Mizoroki-Heck reactions of aryl halides or pseudo-halides with the fluorinated alkenes, and the second part discusses the Pd-catalyzed Mizoroki-Heck reactions of the fluorinated halides or pseudo-halides with alkenes. Variants of the Pd-catalyzed Mizoroki-Heck reactions with fluorine-containing reagents are also briefly depicted. This work supplies an overview, as well as a guide, to both younger and more established researchers in order to attract more attention and contributions in the realm of Mizoroki-Heck reactions with fluorine-containing participants.

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Section: Fluorine-containing Vinyl Sulfur Compounds As the Cross-coupmentioning

confidence: 99%

Section: Fluorine-containing Vinyl Sulfur Compounds As the Cross-coupmentioning

confidence: 99%

“…They found that a combination of catalytic Pd(OAc) 2 with a stoichiometric amount of silver(I) trifluoroacetate enabled the coupling process between either an (hetero)aryl or alkenyl iodide (53 or 55) and ethenesulfonyl fluoride (ESF, 51). The reaction was demonstrated in the successful synthesis of eighty-eight compounds in up to 99% yields, including the unprecedented 2-heteroarylethenesulfonyl fluorides and 1,3-dienylsulfonyl fluorides [61]. These substituted ethenesulfonyl fluorides are useful building blocks for consequent synthetic transformations [61].…”

Section: Fluorine-containing Vinyl Sulfur Compounds As the Cross-coupmentioning

confidence: 99%