Carboxylate Anions Accelerate Pyrrolidinopyridine (PPy)-Catalyzed Acylation: Catalytic Site-Selective Acylation of a Carbohydrate by in Situ Counteranion Exchange

Acylpyridinium ions have been known as catalytically active species in acylation reactions catalyzed by 4-dimethyl­amino­pyridine and its analogues. Acylpyridinium carboxylates were found to be 800–1300 times more reactive than the corresponding acylpyridinium chlorides. A catalytic cycle was develo...

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Published in:Organic letters 2017-06, Vol.19 (12), p.3099-3102
Main Authors: Yanagi, Masanori, Imayoshi, Ayumi, Ueda, Yoshihiro, Furuta, Takumi, Kawabata, Takeo
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cited_by cdi_FETCH-LOGICAL-a411t-130527dae677ec7ce9a2c45551dd94ba2b5449d982424d68a82ffb3388d190c03
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container_title Organic letters
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description Acylpyridinium ions have been known as catalytically active species in acylation reactions catalyzed by 4-dimethyl­amino­pyridine and its analogues. Acylpyridinium carboxylates were found to be 800–1300 times more reactive than the corresponding acylpyridinium chlorides. A catalytic cycle was developed, in which acylpyridinium carboxylates were generated by in situ counteranion exchange from the acylpyridinium chlorides. A catalyst loading as low as 0.01 mol % and catalyst turnover number of up to 6700 were achieved for site-selective acylation of a carbohydrate.
doi_str_mv 10.1021/acs.orglett.7b01213
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title Carboxylate Anions Accelerate Pyrrolidinopyridine (PPy)-Catalyzed Acylation: Catalytic Site-Selective Acylation of a Carbohydrate by in Situ Counteranion Exchange
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