N n diisopropylethylamine dipea

Tomato powder (Kagome Tomato Powder; lycopene content＝241.9 mg/100 g, total Z-isomer ratio of lycopene ＝5.3％, moisture content＝6.9％, average particle size＝ 275.9 μm) was purchased from Kagome Co., Ltd. (Tokyo, Japan) ( Fig. S1) . This tomato powder was produced by drying and grinding Italian tomato paste. Analytical-grade acetone and ethanol were purchased from Kanto Chemical Co., Inc. (Tokyo, Japan) , and high-performance liquid chromatography (HPLC) -grade hexane was purchased from Fujifilm Wako Pure Chemical Corp. (Osaka, Japan) . N,N-Diisopropylethylamine (DIPEA) was purchased from Tokyo Chemical Industry Co., Ltd. (Tokyo, Japan) . Carbon dioxide (＞99.5％ purity) was obtained from Daiwa Corp. (Nagoya, Japan) .

DIB-ET was synthesized in our laboratory according to the previously reported method by our research group. 12 Bromobenzene, o-bromoanisole, p-bromoanisole, o-bromotoluene, p-bromotoluene, p-chloroanisole, p-chlorotoluene, N,Ndiisopropylethylamine (DIPEA), iodobenzene, p-iodoanisole and p-iodotoluene were purchased from Tokyo Chemical Industries (Tokyo). Chrolobenzene, tris{tris[3,5-bis(trifluoromethyl)phenyl]phosphine}palladium (super stable Pd catalyst), 1,4-dioxane, and o-iodoanisole were from Wako (Tokyo). m-Bromoanisole, copper (I) iodide (CuI) and acetonitrile were from Kanto Chemical (Tokyo). m-Bromotoluene was purchased from Sigma (St. Louis, MO). All of the used chemicals were of the highest purity and quality available, while the purities of the tested aryl halide were 98%, excluding Bromobenzene (99%) and p-bromoanisole (97%).
The synthesis and characterization of the aryl halides authentic derivatives of DIB-ET are described in Supporting Information.
Aryl halides standard solutions, DIB-ET (3.0 mM), super stable Pd (2.5 mM), CuI (0.5 mM) and DIPEA (50 mM) reagent solutions were prepared in dioxane.