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

• DOI: 10.1021/acs.orglett.3c01663
• Publication Date: 2023-07-24T16:18:21Z
• Authors: Arun D. R. Shada; Hari P. R. Mangunuru; Leila Terrab; Srinivasarao Tenneti; Nageswara Rao Kal...; Santhosh Reddy Naini; Praveen Gajula; Emily B. Crull; Venumadhav Janganati; Raghavendra Kovvuri; Vasudevan Natarajan; Daniel Lee; Jinya Yin; Lalith Samankumara; Rohit Mahar; Xueyi Zhang; Anji Chen; Chathuranga C. He...; Zhirui Wang; Manasa Mamunooru; Jagruti Rana; Chaitanya S. Wannere; Joseph D. Armstrong; R. Thomas Williamson; Gopal Sirasani; Bo Qu; Chris H. Senanayake
• Keywords: Aqueous medium; Suzuki reaction; Coupling reaction

We report a new class of highly effective, benzooxaphosphole-based, water-soluble ligands in the application Suzuki–Miyaura cross-coupling reactions for sterically hindered substrates aqueous media. The catalytic activities coupling were greatly enhanced by addition amounts organic phase transfer reagents, such as tetraglyme and tetrabutylammonium bromide. optimized general protocol can be conducted with low catalyst load, thereby providing practical solution these reactions. viability this was demonstrated various to generate important building blocks, including heterocycles, synthesis biologically active compounds.