Copper-catalyzed radical approach to allenyl iodides

Song, Yulong; Song, Sanghoon; Duan, Xinyu; Wu, Xiaoyan; Feng, Jianying; Zhang, Yuchen; Fan, Junjie; Huang, Xin; Fu, Chunling; Ma, Shengming

doi:10.1039/c9cc05853b

Cited by 49 publications

(27 citation statements)

References 71 publications

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“…In 2021, the Liu group reported a copper-catalyzed radical asymmetric 1,4-carboalkynylation of 1,3-enynes with terminal alkynes (Figure b), which offers an efficient method for the synthesis of alkyne-containing tetrasubstituted chiral allenes. In addition, there are also several 1,4-difunctionalization reactions of 1,3-enynes realized by the groups of Bao, Wang, Li, and others . Despite these promising advances, a new method for producing multisubstituted allene derivatives with greater functional group tolerance and improved molecular diversity is still highly desired.…”

Section: Introductionsupporting

confidence: 59%

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Copper-Catalyzed Direct Allenylation of Inactive Cyclic Ethers

et al. 2021

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We report here a direct allenylation reaction of inactive cyclic ethers. The reaction proceeds through a copper-catalyzed 1,4-difunctionalization of 1,3-enynes, with cyano group installed at the allenes simultaneously. This methodology shows a broad functional group compatibility to 1,3-enynes. Diversified allene-modified cyclic ether derivatives were synthesized with high regioselectivity under mild conditions.

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Section: Introductionsupporting

confidence: 59%

“…On the basis of above experimental results and previous reports, ,, a plausible mechanism is proposed (Scheme ). Initially, the LCu(I) species A reacts with TBHP to afford the LCu(II)OH species B and a t- BuO radical C via a single electron transfer process.…”

Section: Results and Discussionmentioning

confidence: 99%

Copper-Catalyzed Direct Allenylation of Inactive Cyclic Ethers

et al. 2021

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“…[31] Ma et al have reported copper(I) catalyzed radical methodology to prepare allenyl iodides from 1,3-enynes. [32] In the presence of catalytic amount of Cu I I, 1,3-enynes 60 react with sulfonyl iodides 61 to form allenyl iodides 62 in high chemical efficiency (Table 2). The reaction showed very good scope with respect to the 1,3-enynes as well as the sulfonyl iodides.…”

Section: Radical Additions To Enynesmentioning

confidence: 99%

Propargyl Radicals in Organic Synthesis

et al. 2021

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The appearance of propargyl radicals as synthetic intermediates has increased in recent years from a structural curiosity to a frequent occurrence. This minireview covers the synthetically relevant organic chemistry involving the intermediacy of propargyl radicals. The review is organized by the process employed in radical generation, including H-atom abstraction, propargyl-X homolyses, radical addition to enynes, reduction of polar C=X bonds, reductions of stable carbocations, and metalmediated coupling reactions. The relevant mechanisms of generation and reaction are discussed, as are applications in syntheses of target molecules of interest.

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“…And then, radical addition of the sulfonyl radical with 1,3enynes affords two resonant radical intermediates: alkyl radical Int-62 and allenyl radical Int-63. 74 Subsequently, the radical cross coupling of allenyl radical Int-63 with the NO radical generates the allenyl intermediate Int- 64, which undergoes successive isomerization and intramolecular nucleophilic cyclization to produce the desired products 119 in the presence of InBr 3 . The authors also demonstrated that InBr 3 plays an important role in this cascade pathway.…”

Section: Indium Catalystsmentioning

confidence: 99%