Intramolecular Ullman-type reaction

As a metal-mediated approach, intramolecular Ullman-type reaction of 2-(2-haloaryl)phenols with copper salts has been used for dibenzofuran synthesis [35]. However, harsh reaction conditions are generally required. On the other hand, Liu et al. developed the copper-mediated intramolecular O-arylation of 2-(2-haloaryl)phenols under milder and neutral conditions [36]. The reaction of 2-(2-chloroaryl)phenols 65 with electron-withdrawing substituent(s) gave the corresponding dibenzofurans 66 in high yields (Scheme 23.25). They also demonstrated the... 

Direct coupling of vinyl halides and phenols under Ullman-type reaction conditions can be useful for the preparation of aryl vinyl ethers, and intramolecular version of this process has been applied to the synthesis of spirocyclic oxindoles through a sequence of intramolecular Ullman coupling and Claisen rearrangement reactions (eq 58). ... 

A Cu-catalyzed, Ullman-type intramolecular arylation of a protected amine afforded l,5-benzodiazepin-2-ones in good yield via a type a ring closure (Scheme 66) <20050L4781>. An 1V-BOC or IV-diisopropylphosphono (DIPP) protecting group was essential for the success of this reaction since unprotected amines failed to cyclize under the same conditions. 

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