Author (Your Name)

Eric Rosenthal, Colby College

Date of Award


Document Type

Honors Thesis (Open Access)


Colby College. Chemistry Dept.


Jeffrey L. Katz

Second Advisor

Dasan Thamattoor


Alkene (6) was produced in three steps from 3-hydroxybenzaldehyde (8), and 3-bromobenzyl bromide (10). A variety of strategies were employed to synthesize the desired boronic acid (13), but as of this time none have been successful. The synthesis of this boronic acid is necessary to study the feasibility of applying the Chan-Evans copper mediated formation of diaryl ethers to a bis(bibenzyl) synthesis. In seeking to exploit the advantages of the Chan-Evans ether synthesis over the Ullman ether synthesis, we have encountered some of the associated difficulties. The utilization of an arylboronic acid to produce a diaryl ether first requires the production of the appropriate boronic acid. This has been shown to be no tri vial task. As our boronic acid (14) is to be derived from a bromide, the copper mediated reaction requires an additional step (conversion of the bromjde to the boronic acid), which would not be necessary if the Ullman ether synthesis were employed. Future work in this group should be directed towards the use of alternative methods of hydrogenating alkene (6). Also, methods need to be further developed to allow for the efficient conversion of the bromide to the boronic acid for this type of system. Further work is required to determine the feasibility of using the Chan-Evans ether synthesis to form bis(bibenzyls).


Ether -- Synthesis

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