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Effective BI‐DIME Ligand for Suzuki–Miyaura Cross‐Coupling Reactions in Water with 500 ppm Palladium Loading and Triton X
Author(s) -
Patel Nitinchandra D.,
Rivalti Daniel,
Buono Frederic G.,
Chatterjee Arindom,
Qu Bo,
Braith Stefan,
Desrosiers JeanNicolas,
Rodriguez Sonia,
Sieber Joshua D.,
Haddad Nizar,
Fandrick Keith R.,
Lee Heewon,
Yee Nathan K.,
Busacca Carl A.,
Senanayake Chris H.
Publication year - 2017
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201700137
Subject(s) - chemistry , palladium , ligand (biochemistry) , catalysis , coupling reaction , solvent , green chemistry , pulmonary surfactant , combinatorial chemistry , organic chemistry , reaction mechanism , biochemistry , receptor
An efficient, sustainable, and broadly applicable procedure has been developed for Suzuki–Miyaura cross‐coupling reactions in environmentally benign solvent (water) by employing as little as 500 ppm Pd(OAc) 2 with a monophosphorus BI‐DIME ligand in the presence of inexpensive and commercially available nonionic surfactant Triton X‐100. This method was applied to a broad range of functionalized reaction partners, thereby affording excellent yields of the coupling products, including active pharmaceutical ingredients (APIs). An interesting kinetic study by using reaction calorimetry is also presented, which describes the effect of reaction parameters that enabled the low catalyst loading.