Catalytic enantioselective synthesis of boron-stereogenic BODIPYs

Zu，Bing1; Guo，Yonghong1; Ren，Li Qing1; Li，Yingzi2; He，Chuan1

2023-06-01

10.1038/s44160-023-00262-1

Nature Synthesis   Impact Factor & Quartile

2731-0582

Boron dipyrromethenes (BODIPYs) are a class of tetracoordinate boron compounds that have attracted considerable interest in recent decades due to their excellent spectroscopic properties and structural versatility, leading to their widespread applications in chemical, biological, pharmaceutical and materials science. However, BODIPYs possessing boron-stereogenic centres in enantioenriched forms are rare and catalytic methodology to enantioselectively prepare a boron-stereogenic BODIPY remains elusive. Here we report a palladium-catalysed protocol for the enantioselective synthesis of boron-stereogenic BODIPYs via a desymmetric intramolecular C–H arylation reaction. This method gives access to a wide range of highly functionalized boron-stereogenic BODIPYs, including six- to nine-membered boron heterocycles, with good to excellent enantioselectivities. The discrimination of the two α C–H bonds of the BODIPY core is enabled by the co-action of steric hindrance and attractive interaction in the catalytic chiral pocket. Photophysical properties, derivatizations and applications in chiral recognition of the obtained chiroptical BODIPYs are investigated. This work enriches the chemical diversity of chiroptical BODIPY dyes. [Figure not available: see fulltext.]

English

First ; Corresponding

Science, Technology and Innovation Commission of Shenzhen Municipality[20200925152450004];National Natural Science Foundation of China-Yunnan Joint Fund[22101120];National Natural Science Foundation of China-Yunnan Joint Fund[22122102];National Natural Science Foundation of China-Yunnan Joint Fund[22271134];Science, Technology and Innovation Commission of Shenzhen Municipality[JCYJ20190809142809370];

2-s2.0-85164892341

Scopus

1.Shenzhen Grubbs Institute and Department of Chemistry,Guangdong Provincial Key Laboratory of Catalysis,Southern University of Science and Technology,Shenzhen,Guangdong,China
2.Department of Chemistry,Colorado State University,Fort Collins,United States

Zu，Bing,Guo，Yonghong,Ren，Li Qing,et al. Catalytic enantioselective synthesis of boron-stereogenic BODIPYs[J]. Nature Synthesis,2023,2(6):564-571.

Zu，Bing,Guo，Yonghong,Ren，Li Qing,Li，Yingzi,&He，Chuan.(2023).Catalytic enantioselective synthesis of boron-stereogenic BODIPYs.Nature Synthesis,2(6),564-571.

Zu，Bing,et al."Catalytic enantioselective synthesis of boron-stereogenic BODIPYs".Nature Synthesis 2.6(2023):564-571.