Question

what bonds are made/broken in the palladium catalyzed reaction of structure 8 and 9 shown below

Organic Letters Scheme 2. Total Synthesis of (---)-Aspergilazine A YNH Pd. (dba) (1 mol %) rac-BINAP (2 mol %) NaOBU (2.0 equiv) PhMe, 70 °C (75% yield) Br (1.0 equiv) (1.2 equiv) TES HN 9 (3 equiv) 0 1. Pd[P('Bu)gla (10 mol %) Cy2NMe, 1,4-dioxane, 80 °C (62% yield) 2. 1 N HCI/MeOH, 23 °C (74% yield) HN (-)-aspergilazine A (10) is a considerably more challenging synthetic undertaking. This highly convergent synthesis proceeds in an overall yield of 21% from commercially available starting materials and underscores the utility of this methodology in the direct preparation of complex molecular scaffolds. In summary, we have developed a mild and general protocol for the Pd-catalyzed synthesis of functionalized tryptophan derivatives. The reaction proceeds with low catalyst loadings, displays excellent substrate scope, and is readily scalable to provide gram quantities of synthetically useful unnatural

and what type if reaction occurs between 8 and 9?

Answer 1

Ans: Carbon iodine bond is broken and carbon nitrogen bond is formed. The above reaction is Buchwald Hartwig coupling. It is a palladium catalyzed reaction.