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Synfacts 2006(8): 0776-0776  
DOI: 10.1055/s-2006-941982
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Regioselective Double Suzuki Cross Coupling of Dibromopyrroles

Contributor(s): Victor Snieckus, Wei Gan
S. T. Handy*, J. J. Sabatini
State University of New York at Binghamton, USA
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Publication History

Publication Date:
21 July 2006 (online)

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Significance

In this report, a sequential, regioselective double Suzuki-Miyaura cross coupling in one pot is established. The electron-withdrawing 2-formyl substituent differentiates coupling at the C4 and C5 bromo centers. N-Alkylation or N-protection is necessary to avoid C4 reductive debromination during the first coupling at C5. Ligands (Ph3P, t-Bu3P/HBF4) are used to facilitate the second coupling at C4.