Alkyl halides, reactions with arene Table

In contrast to the IIT mechanism, the clement effect on the Arens path is expected to be A (I) > A (Br) > A (C1) as is also the case with S 2 reactions of alkyl halides (Table 25) . This reactivity order has been observed in the reactions of l-halo-2-(2-thienyDacetylenes with sulphides and thiolates in methanol-water in which the C—X bond is presumably broken in the rate-determining step by attack on halogen (see Section Il.C.l.d). In both 5 n2 and halogen abstraction reactions, the magnitude of the element effect is quite large (Table 25). 

Under our optimized conditions (Table 2, entry 6 Table 3, entries 3 and 10), the generality of the reaction was investigated with respect to both the indole and the arene coupling partner. Substitution at both C5 and C6 was tolerated in the form of electron-donating groups (methoxy), halides (Cl), alkyl groups (methyl),... 

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