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Copper‐Catalyzed Three‐Component Borylstannylation of Alkynes
Author(s) -
Takemoto Yuki,
Yoshida Hiroto,
Takaki Ken
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201202435
Subject(s) - stille reaction , chemistry , catalysis , tin , copper , coupling reaction , alkoxide , triple bond , carbon–carbon bond , transmetalation , carbon fibers , regioselectivity , polymer chemistry , organic chemistry , medicinal chemistry , double bond , materials science , composite number , composite material
Regio‐ and stereoselective installation of boryl and stannyl moieties into a carbon–carbon triple bond of various alkynes has been achieved based on a three‐component coupling reaction by using a diboron and a tin alkoxide with the aid of a copper(II) acetate–tricyclohexylphosphine complex, giving diverse vic ‐borylstannylalkenes in a straightforward manner. Carbon–tin and carbon–boron bonds of the resulting borylstannylation product are successively transformed into carbon–carbon bonds by a Migita–Kosugi–Stille and a Suzuki–Miyaura coupling, leading to the formation of ( Z )‐tamoxifen with anti‐breast cancer activity.