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Efficient and Selective Methane Borylation Through Pore Size Tuning of Hybrid Porous Organic-Polymer-Based Iridium Catalysts

Qi Chen, Anwang Dong, Dongxu Wang, Lu Qiu, Chunxin Ma, Yihui Yuan, Yunpeng Zhao, Na Jia, Zhanhu Guo, Ning Wang

Angew Chem Int Ed Engl. 2019 Jul 29;58(31):10671-10676.

PMID: 31144424

Abstract:

As a new energy source that could replace petroleum, the global reserves of methane hydrate (combustible ice) are estimated to be approximately 20 000 trillion cubic meters. A large amount of methane hydrate has been found under the seabed, but the transportation and storage of methane gas far from coastlines are technically unfeasible and expensive. The direct conversion of methane into value-added chemicals and liquid fuels is highly desirable but remains challenging. Herein, we prepare a series of iridium complexes based on porous polycarbazoles with high specific areas and good thermochemical stabilities. Through structure tuning we optimized their catalytic activities for the selective monoborylation of methane. One of these catalysts (CAL-3-Ir) can produce methyl boronic acid pinacol ester (CH3 Bpin) in 29 % yield in 9 h with a turnover frequency (TOF) of approximately 14 h-1 . Because its pore sizes favor monoborylated products, it has a high chemoselectivity for monoborylation (CH3 Bpin:CH2 (Bpin)2 =16:1).

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
LS793421 methyl 3-amino-5-boronobenzoate, pinacol ester methyl 3-amino-5-boronobenzoate, pinacol ester Price
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