Nickel‐Catalyzed Enantioselective Conjunctive Cross‐Coupling of 9‐BBN Borates

Chierchia, Matteo; Law, Chunyin; Morken, James P.

doi:10.1002/ange.201706719

Cited by 36 publications

(4 citation statements)

References 65 publications

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“…In 2017, the Morken group reported a nickel‐catalyzed enantioselective arylalkylation of alkylvinyl borates with chiral diamine as the ligand (Scheme 38a). [ 96 ] Chiral 9‐BBN derivatives were obtained with high enantioselectivities through this approach, which could be efficiently converted to the chiral alcohols. The chiral 9‐BBN could also serve as a versatile…”

Section: Intermolecular Dicarbofunctionalization Of Alkenesmentioning

confidence: 99%

Nickel‐CatalyzedDicarbofunctionalization of Alkenes^†

2020

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As a straightforward strategy for rapidly increasing molecular complexity, dicarbofunctionalization of alkenes has attracted substantial interests of organic synthesis, medicine chemistry, and materials science. Nickel-catalyzed cascade dicarbofunctionalizations have been flourished in this area recently, and nickel-mediated radical pathways particularly offer new opportunities in conjunctive cross-couplings with alkyl coupling partners. Herein, we give a comprehensive review of nickel-catalyzed dicarbofunctionalization of alkenes through a historical perspective, including intermolecular three-component reactions and intramolecular cascade reactions. Among the pathways discussed in this review, the carbometallation/cross-coupling process and the radical addition/cross-coupling process are the two major pathways for the nickel-catalyzed dicarbofunctionalization of alkenes. The oxidative cyclization and 1,2-metallate shift processes are also selectively discussed. These methods overcome the limitations associated with the reactions using noble metals in the field, providing an efficient and straightforward access to structurally diversified molecules. Yun-Cheng Luo (right) received his BSc degree in 2016 and master degree in 2019 from University of Science and Technology of China. Then he joined Professor Xingang Zhang's group at Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences to pursue his doctorate in organic chemistry. His research interests are focused on the activation of inert C-H or C-X bonds of bulky chemicals and their applications in the synthesis of fluorine-containing compounds. Chang Xu (middle) obtained his BSc degree in basic pharmacy from China Pharmaceutical University (China) in 2015. With an interest in organic chemistry and medicinal chemistry, he then began his graduate studies at Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences under the supervision of Professor Xingang Zhang. His research interests are focused on the activation and transformations of fluoroalkylanes and their applications in medicinal chemistry. Xingang Zhang (left) obtained his BSc degree in 1998 from Sichuan University (China) and received the Ph.D. in 2003 at Shanghai Institute of Organic Chemistry (SIOC), Chinese Academy of Sciences. After his postdoctoral work at University of Illinois at Urbana Champaign (USA), he joined the faculty team of SIOC as a research associate professor in 2008, and became research professor in 2012. His current research interests are focused on organofluorine chemistry and chemical biology.

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Section: Intermolecular Dicarbofunctionalization Of Alkenesmentioning

confidence: 99%

Nickel‐CatalyzedDicarbofunctionalization of Alkenes^†

2020

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“…In addition, we investigated stoichiometric reactions with phenylnickel(II) iodide Aa, which was prepared from Ni(cod) 2 , 2,2'-bpy, and iodobenzene (2 a) after purification according to the procedure found in the literature (Scheme 5). [12] Phenylnickel(II) iodide Aa underwent the defluorinative coupling with 1 a in the presence of Et 3 SiCl without Mn to afford 3 aa in 28 % yield (Scheme 5a). When 2 f bearing an electronwithdrawing ester group was added under the same conditions, a small amount (8 %) of 3 af derived from 1 a and 2 f was obtained along with 3 aa (32 %) (Scheme 5b).…”

Section: Chemistry-a European Journalmentioning

confidence: 99%

Nickel‐Catalyzed Reductive Allyl−Aryl Cross‐Electrophile Coupling via Allylic C−F Bond Activation

Fujita

Kobayashi

Takahashi

et al. 2021

Chemistry A European J

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Nickel-catalyzed reductive cross-coupling of allylic difluorides with aryl iodides was achieved via allylic CÀ F bond activation. Based on this protocol, a series of γ-arylated monofluoroalkenes were synthesized in moderate to high yields with high Z-selectivities. Mechanistic studies suggest that the CÀ I bonds of the aryl iodides and the CÀ F bonds of the allylic difluorides were cleaved via oxidative addition and β-fluorine elimination, respectively, where the oxidative addition of less reactive CÀ F bonds was avoided to permit their transformation.

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“…With these modifications,3 -phenylpropyl (10)a nd n-octyl (11)m igrating groups were tolerated, as was asilyl ether (12). Ther eaction was also effective with cyclic substrates,including cyclopentyl (13), cyclohexyl (14), and N-Boc-protected piperidine (15) migrating groups.Migrating groups bearing potentially sensitive functional groups such as am onosubstituted olefin (16), amide (17), ester (18), or acetal (19)were also well-tolerated in this reaction. While examples in Table 2s uggest that the reaction is effective with Grignard-derived "ate" complexes, it should be noted that alkyllithium derived "ate" complexes often offer superior reactivity such that catalyst loading can be reduced to 1mol %Pd, with many substrates still achieving complete conversion in one hour (10)(11)(12).…”

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confidence: 99%

“…[14] Recently,w ed eveloped Pd-catalyzed conjunctive crosscoupling reactions between an organoboronic ester,avinyllithium reagent, and aC (sp 2 )t riflate to give chiral organoboronic esters with high levels of enantiopurity. [15] This reaction has been expanded to include the use of Grignard reagents and C(sp 2 )halide electrophiles, [16] alkenyl migrating groups, [17] and has extended to nickel catalysts with both aryl [18] and alkyl electrophiles. [19] Perhaps unsurprisingly, direct extension to allyl electrophiles has proved achallenge, likely because h 3 coordination of the allyl group occupies acoordination site necessary for binding and activation of the "ate" complex.…”

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confidence: 99%