A patent was issued this month that reminds us that phase-transfer catalysis facilitates various coupling reactions catalyzed by transition metal complexes such as those containing palladium.
More than a dozen coupling reactions catalyzed by tetrabutylammonium bromide or chloride and tetrakis(triphenylphosphine)palladium were described in detail. Some of the coupling reactions were Suzuki. The diagram shows two examples. The ratio between the quaternary ammonium phase-transfer catalyst and the tetrakis(triphenylphosphine)palladium catalyst, varies from application to application.
We are not aware of reports that definitively elucidate the role of the quaternary ammonium phase-transfer catalyst in reactions catalyzed by palladium. However, Dr. Peter Wuts has offered input about the co-catalytic effect of quat salts and palladium complexes in Suzuki reactions that contain water. You can read Dr. Wuts’ input at http://phasetransfercatalysis.com/ptc_tip/alternative-explanation-for-ptc-suzuki/.
About Marc Halpern
Dr. Halpern is founder and president of PTC Organics, Inc., the only company dedicated exclusively to developing low-cost high-performance green chemistry processes for the manufacture of organic chemicals using Phase Transfer Catalysis. Dr. Halpern has innovated PTC breakthroughs for pharmaceuticals, agrochemicals, petrochemicals, monomers, polymers, flavors & fragrances, dyes & pigments and solvents. Dr. Halpern has provided PTC services on-site at more than 260 industrial process R&D departments in 37 countries and has helped chemical companies save > $200 million. Dr. Halpern co-authored five books including the best-selling “Phase-Transfer Catalysis: Fundamentals, Applications and Industrial Perspectives” and has presented the 2-day course “Practical Phase-Transfer Catalysis” at 50 locations in the US, Europe and Asia.
Dr. Halpern founded the journal “Industrial Phase-Transfer Catalysis” and “The PTC Tip of the Month” enjoyed by 2,100 qualified subscribers, now beyond 130 issues. In 2014, Dr. Halpern is celebrating his 30th year in the chemical industry, including serving as a process chemist at Dow Chemical, a supervisor of process chemistry at ICI, Director of R&D at Sybron Chemicals and founder and president of PTC Organics Inc. (15 years) and PTC Communications Inc. (20 years). Dr. Halpern also co-founded PTC Interface Inc. in 1989 and PTC Value Recovery Inc. in 1999. His academic breakthroughs include the PTC pKa Guidelines, the q-value for quat accessibility and he has achieved industrial PTC breakthroughs for a dozen strong base reactions as well as esterifications, transesterifications, epoxidations and chloromethylations plus contributed to more than 100 other industrial PTC process development projects.
Dr. Halpern has dedicated his adult life to his family and to phase-transfer catalysis (in that order!).
