1,2-Boryl Migration Empowers Regiodivergent Synthesis of Borylated Furans | Zendy

Roohollah Kazem Shiroodi | Zendy; Olesja Koleda | Zendy; Vladimir Gevorgyan | Zendy

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1,2-Boryl Migration Empowers Regiodivergent Synthesis of Borylated Furans

Author(s) -

Roohollah Kazem Shiroodi,

Olesja Koleda,

Vladimir Gevorgyan

Publication year - 2014

Publication title -

journal of the american chemical society

Language(s) - Uncategorized

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/ja507054j

Subject(s) - chemistry , cycloisomerization , furan , cationic polymerization , regioselectivity , catalysis , counterion , trifluoromethanesulfonate , medicinal chemistry , combinatorial chemistry , organic chemistry , ion

A regioselective transition metal-catalyzed cycloisomerization reaction of boron-containing alkynyl epoxides toward C2- and C3-borylated furans has been developed. It was found that the copper catalyst as well as the gold catalyst with more basic triflate counterion favor boryl migration toward C3-borylated furans, whereas employment of the cationic gold hexafluoroantimonate affords C2-borylated furan via a formal 1,2-hydrogen shift.

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