Chapter 5.1 Five-membered ring systems

Pelkey, Erin T.

doi:10.1016/s0959-6380(98)80007-x

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“…Polyfunctionalized thiophenes are of interest in research fields such as natural product synthesis, drug design, and material science . Therefore, the ready availability of suitable precursors such as disubstituted thiophenes is of great importance.…”

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confidence: 99%

Synthesis of 2,3-Substituted Thienylboronic Acids and Esters

et al. 2003

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A noncryogenic protocol for the synthesis of 2-substituted 3-thienylboronic acids and esters as well as 3-substituted 2-thienylboronic acids and esters has been developed. Electrophiles were introduced regiospecifically in the 2-position of 2,3-dibromothiophene and in the 3-position of 2-bromo-3-iodothiophene by halogen-magnesium exchange followed by quenching with electrophiles. Palladium-catalyzed borylation of the 2,3-substituted halothiophenes with pinacolborane and P(t-Bu)3 as ligand for Pd produced 9 and 10. The borylation protocol was tolerated by a range of functional groups; however, strongly electron-withdrawing substituents decreased the stability of the thienylboronic acids and esters.

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confidence: 99%