2-Iodo-1-C-acceptor-substituted glycals: synthesis and transformation into 1,2-C,C-disubstituted glycals via Suzuki–Miyaura coupling reaction

Juhász-Tóth, Éva; Szilárd Malecz, Ádám; Tóth, Marietta; Homolya, Ágnes; Kaszás, Tímea; Somsák, László; Juhász, László

doi:10.1039/d3nj03119e

Cited by 1 publication

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References 30 publications

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“…That was particularly puzzling, since the peracetylated compounds have already been used as reagents in similar transformations: carbonylative SM, [47] or quite recently, cross-coupling of glycals with the electron withdrawing groups at the pseudoanomeric position. [70] Considering all of that the route to succeed with our goals became quite clear. We decided to develop at first reliable protocol of SM reaction compatible with the most accessible glycals -peracetylated ones.…”

Section: Introductionmentioning

confidence: 96%

Suzuki‐Miyaura Reaction of Glycals with Base‐Labile Protecting Groups as a New Route to Glycoporphyrins

Godlewski,

Malinowski

2024

Adv Synth Catal

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Glycoporphyrins are considered promising photosensitisers of new generation. Herein, we describe the original, metal‐catalysed method towards porphyrin‐carbohydrate C‐C conjugates. The protocol of Suzuki‐Miyaura reaction has been developed and it was compatible with peracetylated 2‐iodoglycals. The utility of the reaction was exemplified on 15 different (C‐2)‐arylated sugar derivatives. Then it was applied on more challenging starting materials, namely, porphyrin boronates in which we addressed the issues of difficult transmetalation step usually observed on palladium‐catalysed processes of porphyrin derivatives. The efficiency of the protocol was finally applied to synthesize the library of glycoporphyrins proving the versatile character of this strategy. Keywords: Suzuki‐Miyaura reaction, glycoporphyrins, photosensitisers, carbohydrates, porphyrins, palladium catalysis, glycal

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Section: Introductionmentioning

confidence: 96%

Suzuki‐Miyaura Reaction of Glycals with Base‐Labile Protecting Groups as a New Route to Glycoporphyrins

Godlewski,

Malinowski

2024

Adv Synth Catal

View full text Add to dashboard Cite

show abstract

2-Iodo-1-C-acceptor-substituted glycals: synthesis and transformation into 1,2-C,C-disubstituted glycals via Suzuki–Miyaura coupling reaction

Abstract: A series of 2-iodo-1-C-substituted glycals having electron withdrawing groups (CN, CO2CH3, CONH2) at the C-1 carbon were synthesized from the parent 1-C-substituted glycals using N-iodosuccinimide or N-iodophtalimide and a Lewis...

Cited by 1 publication

References 30 publications

Suzuki‐Miyaura Reaction of Glycals with Base‐Labile Protecting Groups as a New Route to Glycoporphyrins

Suzuki‐Miyaura Reaction of Glycals with Base‐Labile Protecting Groups as a New Route to Glycoporphyrins

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