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Ir-catalyzed C-H borylation is found to be compatible with Boc protecting groups. Thus, pyrroles, indoles, and azaindoles can be selectively functionalized at C-H positions beta to N. The Boc group can be removed on thermolysis or left intact during subsequent transformations.


Venkata A Kallepalli, Feng Shi, Sulagna Paul, Edith N Onyeozili, Robert E Maleczka, Milton R Smith. Boc groups as protectors and directors for Ir-catalyzed C-H borylation of heterocycles. The Journal of organic chemistry. 2009 Dec 4;74(23):9199-201

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PMID: 19894699

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