Fig. 5: Preparation of densely functionalized arenes. | Nature Communications

Fig. 5: Preparation of densely functionalized arenes.

From: 3-sulfonyloxyaryl(mesityl)iodonium triflates as 1,2-benzdiyne precursors with activation via ortho-deprotonative elimination strategy

Fig. 5

a Cascade reactions with 6. b Cascade nucleophilic-one reactions with 14. c Cascade nucleophilic, [4 + 2]-cycloaddition reactions with 18. d Reactions with N-benzoylbenzamide. Reaction conditions: [a] Slow addition of a solution of 1 (0.4 mmol) in 1,4-dioxane (3 mL) to a suspension of benzothioamide 6 (0.2 mmol), Cs2CO3 (1.6 mmol), and 18-c-6 (0.4 mmol) in 1,4-dioxane (3 mL) at 80 oC over 3 hours. [b] Slow addition of a solution of 1-TS (0.4 mmol) in chlorobenzene (3 mL) to a suspension of tosylamide 14 (0.2 mmol), Cs2CO3 (1.6 mmol), and 18-c-6 (0.4 mmol) in chlorobenzene (3 mL) at 130 oC over 3 hours. [c] Slow addition of a solution of 1-FPs (0.4 mmol) in MeCN (7 mL) to a suspension of cinnamyl amide 18 (0.2 mmol), Cs2CO3 (1.2 mmol), and 18-c-6 (0.1 mmol) in toluene (7 mL) at 100 oC over 4 hours. [d] Slow addition of a solution of 1 (0.8 mmol) in acetonitrile (5 mL) to a suspension of N-benzoylbenzamide (0.4 mmol), Cs2CO3 (1.6 mmol), water (0.08 mmol), and 18-c-6 (0.2 mmol) in acetonitrile (5 mL) at 80 oC over 8 hours.

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