Design and Discovery of Water-Soluble Benzooxaphosphole-Based Ligands for Hindered Suzuki–Miyaura Coupling Reactions with Low Catalyst Load

We report a new class of highly effective, benzooxaphosphole-based, water-soluble ligands in the application of Suzuki–Miyaura cross-coupling reactions for sterically hindered substrates in aqueous media. The catalytic activities of the coupling reactions were greatly enhanced by the addition of cat...

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Published in:Organic letters 2024-04, Vol.26 (14), p.2751-2757
Main Authors: Shada, Arun D. R., Mangunuru, Hari P. R., Terrab, Leila, Tenneti, Srinivasarao, Kalikinidi, Nageswara Rao, Naini, Santhosh Reddy, Gajula, Praveen, Crull, Emily B., Janganati, Venumadhav, Kovvuri, Raghavendra, Natarajan, Vasudevan, Lee, Daniel, Yin, Jinya, Samankumara, Lalith, Mahar, Rohit, Zhang, Xueyi, Chen, Anji, Hewa-Rahinduwage, Chathuranga C., Wang, Zhirui, Mamunooru, Manasa, Rana, Jagruti, Wannere, Chaitanya S., Armstrong, Joseph D., Williamson, R. Thomas, Sirasani, Gopal, Qu, Bo, Senanayake, Chris H.
Format: Article
Language:English
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Summary:We report a new class of highly effective, benzooxaphosphole-based, water-soluble ligands in the application of Suzuki–Miyaura cross-coupling reactions for sterically hindered substrates in aqueous media. The catalytic activities of the coupling reactions were greatly enhanced by the addition of catalytic amounts of organic phase transfer reagents, such as tetraglyme and tetrabutylammonium bromide. The optimized general protocol can be conducted with a low catalyst load, thereby providing a practical solution for these reactions. The viability of this new Suzuki–Miyaura protocol was demonstrated with various substrates to generate important building blocks, including heterocycles, for the synthesis of biologically active compounds.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c01663