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An efficient Nozaki-Hiyama allenylation promoted by the acid derived MIL-101 MOF.

ABSTRACT: A concise synthesis of the sulfonic acid-containing MIL-101 MOF catalyst was reported using commercially available materials. A series of characterization of as-synthesized MIL-101-SO₃H including SEM, XRD, FTIR, BET and TGA was also demonstrated. Using MIL-101-SO₃H as a catalyst, an efficient Nozaki-Hiyama allenylation reaction was achieved to generate various polyfunctionalized α-allenic alcohols in high yield and good selectivity. Taking advantage of the high acidity of the MIL-101-SO₃H MOF structure, such transformations were also achieved under mild reaction conditions and short reaction times. Based on our observed evidence during this study, a mechanism was proposed involving a substrate activation/γ-nucleophilic addition reaction sequence. In addition, the MIL-101-SO₃H catalyst can be recycled ten times during the Nozaki-Hiyama allenylation reaction without compromising the yield and selectivity.

SUBMITTER: Luan Y

PROVIDER: S-EPMC9061183 | biostudies-literature | 2019 Mar

REPOSITORIES: biostudies-literature

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An efficient Nozaki-Hiyama allenylation promoted by the acid derived MIL-101 MOF.

Luan Yi Y Cai Zonghui Z Li Xiujuan X Ramella Daniele D Miao Zongcheng Z Wang Wenyu W

RSC advances 20190307 13

A concise synthesis of the sulfonic acid-containing MIL-101 MOF catalyst was reported using commercially available materials. A series of characterization of as-synthesized MIL-101-SO<sub>3</sub>H including SEM, XRD, FTIR, BET and TGA was also demonstrated. Using MIL-101-SO<sub>3</sub>H as a catalyst, an efficient Nozaki-Hiyama allenylation reaction was achieved to generate various polyfunctionalized α-allenic alcohols in high yield and good selectivity. Taking advantage of the high acidity of t ...[more]

PMID: 35519953

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