1 Supplemental Information Pd-Catalyzed Suzuki Coupling Reactions of Aryl Halides Containing Basic Nitrogen Centers with Arylboronic Acids in Water in the Absence of Added Base Zhao Li, a Carol Gelbaum, a Zachary S. Campbell, b Paul C Gould, a Jason S. Fisk, c Bruce Holden, c Arvind Jaganathan, d Gregory T. Whiteker, d Pamela Pollet, a and Charles L. Liotta* ,a,b a School of Chemistry and Biochemistry, Georgia Institute of Technology, Atlanta, Georgia 30332, USA b School of Chemical and Biomolecular Engineering, Georgia Institute of Technology, Atlanta, Georgia 30332, USA c The Dow Chemical Company, Midland, Michigan 48674, USA d Dow AgroSciences, Indianapolis, Indiana 46268, USA Content Page S1 Comparison of reaction yields determined by various analytical methods employing 2- amino-6-chloropyridine as a model substrate………………………………………………… 2 S2 Experimental procedure……………………………………………………………………… 3 S3 GC analysis…………………………………………………………………………………… 4 S4 NMR analysis………………………………………………………………………………… 6 S5 Isolation of product…………………………………………………………………………… 7 S6 Comparison of the yields determined by GC-FID and 1 H NMR for the aryl bromides and aryl chlorides from Table 1 in the main manuscript. ………………………………………… 8 S7 Comparison of the yields determined by GC-FID and 1 H NMR for the aryl chlorides from Table 3 in the main manuscript……………………… ……………………………………… 9 S8 Comparison of the yields determined by GC-FID and 1 H NMR for the arylboronic acids from Table 5 in the main manuscript………………………………………………………… 10 S9 Suzuki reactions in buffered acidic media: the Pd(OAc)2–PtB catalyzed Suzuki reaction of 4-chlorobenzyl amine with PhB(OH)2 in phosphate-buffered acidic solutions……………… 12 S10 The ligand-free Pd(OAc)2 catalyzed Suzuki reaction of 4-amino-2-chloropyridine with PhB(OH)2 in phosphate-buffered acidic solutions…………………………………………… 13 S11 The ligand-free Pd(OAc)2 catalyzed Suzuki reaction of 4-amino-2-bromopyridine with PhB(OH)2 in phosphate-buffered acidic solutions…………………………………………… 14 S12 1 H and 13 C NMR spectra of synthesized compounds and isolated products………………… 15 S13 Mass spectral spectra of isolated products…………………………………………………… 47 S14 NMR spectroscopic data for the products (5-7) that have not been successfully isolated…… 77 Electronic Supplementary Material (ESI) for New Journal of Chemistry. This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017