Nickel-catalyzed cross-coupling of chromene acetals and boronic acids

TY - JOUR

T1 - Nickel-catalyzed cross-coupling of chromene acetals and boronic acids

AU - Graham, Thomas J.A.

AU - Doyle, Abigail G.

PY - 2012/3/16

Y1 - 2012/3/16

N2 - A modular and highly efficient protocol for the synthesis of 2-aryl- and heteroaryl-2H-chromenes is described. Under base-free conditions, readily accessible 2-ethoxy-2H-chromenes undergo C sp3-O activation and C sp3-C bond formation in the presence of an inexpensive nickel catalyst and boronic acids. This new strategy enables broad access to 2-substituted-2H-chromenes and has been applied to the late-stage incorporation of complex molecules, including the pharmaceuticals loratidine and indomethacin methyl ester.

AB - A modular and highly efficient protocol for the synthesis of 2-aryl- and heteroaryl-2H-chromenes is described. Under base-free conditions, readily accessible 2-ethoxy-2H-chromenes undergo C sp3-O activation and C sp3-C bond formation in the presence of an inexpensive nickel catalyst and boronic acids. This new strategy enables broad access to 2-substituted-2H-chromenes and has been applied to the late-stage incorporation of complex molecules, including the pharmaceuticals loratidine and indomethacin methyl ester.

UR - https://www.scopus.com/pages/publications/84858692526

UR - https://www.scopus.com/pages/publications/84858692526#tab=citedBy

U2 - 10.1021/ol300364s

DO - 10.1021/ol300364s

M3 - Article

C2 - 22385385

SN - 1523-7060

VL - 14

SP - 1616

EP - 1619

JO - Organic letters

JF - Organic letters

IS - 6

ER -