One‐Pot Palladium‐Catalyzed Cross‐Coupling Treble of Borylation, the Suzuki Reaction and Amination. Issue 4 (26th January 2017)

• Record Type: Journal Article
• Authors: Jong, Howard; Eey, Stanley T.‐C.; Lim, Yee Hwee; Pandey, Sangeeta; Iqbal, Nurul Azmah Bte; Yong, Fui Fong; Robins, Edward G.; Johannes, Charles W.
• Is Part Of: Advanced synthesis & catalysis. Volume 359:Issue 4(2017)
• Page Start: 616
• Page End: 622
• Publication Date: 2017-01-26
• Subjects: amination -- borylation -- cross-coupling -- one-pot procedure -- palladium -- Suzuki reaction; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201600708
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: A methodology for a sequential palladium‐catalyzed cross‐coupling procedure consisting of borylation, the Suzuki reaction and amination has been developed for the assembly of molecules with multi‐aryl backbones. The linchpin of this development is the meta ‐terarylphosphine ligand, Cy*Phine, which has been employed as an air‐ and moisture‐stable precatalyst, Pd(Cy*Phine)2 Cl2, to improve the efficiency of one‐pot borylation–Suzuki reactions. Additionally, the reactivity of the Pd‐Cy*Phine system could be tuned to furnish a one‐pot, borylation–Suzuki reaction–amination (BSA) cross‐coupling treble. The methodology successfully integrated complementary conditions for three distinctly different and modular reactions. Average yields of 74–94% could be achieved for each segment that cumulatively afforded 50–84% yield over the entire three‐step sequence in a single pot. Abstract :