Recent Strategies for Carbon−Halogen Bond Formation Using Nickel

Marchese, Austin D.; Adrianov, Timur; Lautens, Mark

doi:10.1002/anie.202101324

Cited by 41 publications

(27 citation statements)

References 84 publications

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“…Further investigation of the reaction led to the discovery that it can be successful in an intramolecular setting (Scheme 3). [8a,b,e] Tethered alkynes could successfully react with the acid chlorides to generate benzofuran products with retention of the acid chloride moiety. Again, a palladium catalyst was used in combination with Xantphos at 125 °C to deliver the product.…”

Section: Resultsmentioning

confidence: 99%

Catalytic Carbochlorocarbonylation of Unsaturated Hydrocarbons via C−COCl Bond Cleavage**

et al. 2021

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Here we report ap alladium-catalysed difunctionalisation of unsaturated CÀCb onds with acid chlorides.F ormally,t he C À COCl bond of an acid chloride is cleaved and added, with complete atom economy,a cross either strained alkenes or atethered alkyne to generate new acid chlorides.The transformation does not require exogenous carbon monoxide, operates under mild conditions,shows agood functional group tolerance,a nd gives the isolated products with excellent stereoselectivity.T he intermolecular reaction tolerates both aryl-and alkenyl-substituted acid chlorides and is successful when carboxylic acids are transformed to the acid chloride in situ. The reaction also shows an example of temperaturedependent stereodivergence which,t ogether with plausible mechanistic pathways, is investigated by DFT calculations. Moreover,w es how that benzofurans can be formed in an intramolecular variant of the reaction. Finally,derivatisation of the products from the intermolecular reaction provides ahighly stereoselective approach for the synthesis of tetrasubstituted cyclopentanes.

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Section: Resultsmentioning

confidence: 99%

Catalytic Carbochlorocarbonylation of Unsaturated Hydrocarbons via C−COCl Bond Cleavage**

et al. 2021

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“…Important progress has been made in this area via atom transfer radical addition (ATRA) reactions of alkynes with organohalides, [9] whilst the majority of these reactions require the use of alkyl halides [10] . In this context, Pd‐catalyzed intramolecular carbohalogenation strategy, disclosed by Lautens and others, has been developed to enable aryl halides or carbamoyl chlorides to couple with tethered alkynes via migratory insertion followed by reductive elimination of C−X bond, leading to selective construction of alkenyl halides with high efficiency (Scheme 1a) [8b,d,11] . Recently, Kurahashi and Matsubara utilized simple nickel complexes to develop two examples of catalytic intermolecular carbohalogenation reaction of internal alkynes with aryl halides, [12] where Ni(III) species was proposed to promote the reductive elimination of C−X bond.…”

Section: Methodsmentioning

confidence: 99%

Metallaphotoredox‐Enabled Intermolecular Carbobromination of Alkynes with Alkenyl Bromides

Jiao

Fan

et al. 2022

Adv Synth Catal

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A regioselective intermolecular carbohalogenation of alkynes with alkenyl bromides enabled by dual photoredox and nickel catalysis is described. This dual protocol enables an atomeconomic access to a wide array of brominated 1,3dienes from simple starting materials. Broad substrate scope and high regioselectivity are observed. The synthetic utility has been demonstrated and preliminary mechanistic studies have been performed to elucidate the reaction pathway.

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“…Catalysis is one of the fundamental pillars of green chemistry, the design of chemical products and processes that reduce or eliminate the use and generation of hazardous substances, as well as increase the atom economy of the reac-tion [9]. Among the transition-metal (TM) catalysts often used, the late transition metals like rhodium [10][11][12][13][14], palladium [15][16][17][18][19], nickel [20][21][22][23], and iridium [24][25][26][27] have taken center stage when it comes to the development of synthetic methodology. Although these late TMs have contributed enormously to the various fields of organic, inorganic, and organometallic chemistry, growing concerns regarding their economic and ecological impacts have risen.…”

Section: Introductionmentioning

confidence: 99%

Iron-catalyzed domino coupling reactions of π-systems

Pounder¹,

Tam²

2021

Beilstein J. Org. Chem.

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The development of environmentally benign, inexpensive, and earth-abundant metal catalysts is desirable from both an ecological and economic standpoint. Certainly, in the past couple decades, iron has become a key player in the development of sustainable coupling chemistry and has become an indispensable tool in organic synthesis. Over the last ten years, organic chemistry has witnessed substantial improvements in efficient synthesis because of domino reactions. These protocols are more atom-economic, produce less waste, and demand less time compared to a classical stepwise reaction. Although iron-catalyzed domino reactions require a mindset that differs from the more routine noble-metal, homogenous iron catalysis they bear the chance to enable coupling reactions that rival that of noble-metal-catalysis. This review provides an overview of iron-catalyzed domino coupling reactions of π-systems. The classifications and reactivity paradigms examined should assist readers and provide guidance for the design of novel domino reactions.

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Recent Strategies for Carbon−Halogen Bond Formation Using Nickel

Cited by 41 publications

References 84 publications

Catalytic Carbochlorocarbonylation of Unsaturated Hydrocarbons via C−COCl Bond Cleavage**

Catalytic Carbochlorocarbonylation of Unsaturated Hydrocarbons via C−COCl Bond Cleavage**

Metallaphotoredox‐Enabled Intermolecular Carbobromination of Alkynes with Alkenyl Bromides

Iron-catalyzed domino coupling reactions of π-systems

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