Remote ether groups-directed regioselective and chemoselective cycloaddition of azides and alkynes

Duan, Xuelun; Zheng, Nan; Li, Ming; Sun, Xinhao; Lin, Zhuye; Qiu, Pan; Song, Wangze

doi:10.1016/j.cclet.2021.05.037

Cited by 11 publications

(2 citation statements)

References 46 publications

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“…It should be noted that 1,6-diynes have rarely been employed in the triazoles synthesis, and to the best of our knowledge, only one publication reported where phenyl group substituted bis(propargylic) ether was used in the synthesis of bis(triazole) by employing copper( ii ) salts and expensive iridium( i ) catalysts. 23 Noteworthy to mention that a few oxazole and triazole derivatives could be achieved by mechanical grinding and shaking methods (ESI Fig. S126–S142†) by using cat.…”

Section: Resultsmentioning

confidence: 99%

Dicationic copper(i) complexes bearing ENE (E = S, Se) pincer ligands; catalytic applications in regioselective cyclization of 1,6-diynes

Das¹,

Sahoo²,

Banjare³

et al. 2023

Dalton Trans.

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Section: Resultsmentioning

confidence: 99%

Dicationic copper(i) complexes bearing ENE (E = S, Se) pincer ligands; catalytic applications in regioselective cyclization of 1,6-diynes

Das¹,

Sahoo²,

Banjare³

et al. 2023

Dalton Trans.

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“…Song and co-workers 129 reported excellent regio- and chemoselective synthesis of 5-ether triazoles 254 and 256 from internal alkynes 253 and 255 with azides 2 and 76 using [Ir(COD)Cl 2 ] 2 catalysts in chloroform at 60 °C for 12–24 h ( Scheme 63 ). Upon further investigation, they found that the yield dramatically decreases with an increase in the steric hindrance.…”

Section: Synthesis Of 123-triazole Via Metal-catalyzed Azide–alkyne C...mentioning

confidence: 99%

Versatile Synthetic Platform for 1,2,3-Triazole Chemistry

Vala

Patel

2022

ACS Omega

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1,2,3-Triazole scaffolds are not obtained in nature, but they are still intensely investigated by synthetic chemists in various fields due to their excellent properties and green synthetic routes. This review will provide a library of all synthetic routes used in the past 21 years to synthesize 1,2,3-triazoles and their derivatives using various metal catalysts (such as Cu, Ni, Ru, Ir, Rh, Pd, Au, Ag, Zn, and Sm), organocatalysts, metal-free as well as solvent- and catalyst-free neat syntheses, along with their mechanistic cycles, recyclability studies, solvent systems, and reaction condition effects on regioselectivity. Constant developments indicate that 1,2,3-triazoles will help lead to future organic synthesis and are useful for creating molecular libraries of various functionalized 1,2,3-triazoles.

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Rhodium‐Catalyzed Remote Borylation of Alkynes and Vinylboronates

2022

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Remote functionalization involving a fascinating chain-walking process has emerged as a powerful strategy for the rapid access to value-added functional molecules from readily available feedstocks. However, the scope of current methods is predominantly limited to mono-and di-substituted alkenes. The remote functionalization of multi-and heteroatom-substituted alkenes is challenging, and the use of alkynes in the chain walking is unexplored. We herein report a rhodium catalyzed remote borylation of internal alkynes, offering an unprecedented reaction mode of alkynes for the preparation of synthetically valuable 1,ndiboronates. The regioselective distal migratory hydroboration of sterically hindered tri-and tetra-substituted vinylboronates is also demonstrated to furnish various multi-boronic esters. Synthetic utilities are highlighted through the selective manipulation of the two boryl groups in products such as the regioselective cross coupling, oxidation, and amination.

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Remote ether groups-directed regioselective and chemoselective cycloaddition of azides and alkynes

Cited by 11 publications

References 46 publications

Dicationic copper(i) complexes bearing ENE (E = S, Se) pincer ligands; catalytic applications in regioselective cyclization of 1,6-diynes

Dicationic copper(i) complexes bearing ENE (E = S, Se) pincer ligands; catalytic applications in regioselective cyclization of 1,6-diynes

Versatile Synthetic Platform for 1,2,3-Triazole Chemistry

Rhodium‐Catalyzed Remote Borylation of Alkynes and Vinylboronates

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