- Homo- and heterocoupling of terminal conjugated enynes: One-pot synthesis of alka-1,7-diene-3,5-diynes and alk-1-ene-3,5-diynes via two types of coupling reaction
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Conjugated dienediynes and enediynes with definite geometry- have been prepared in a one-pot manner. This protocol involves two types of coupling reaction, a Suzuki-type coupling and either a Hay coupling or a Cadiot-Chodkiewicz coupling. Thus, the copper
- Hoshi, Masayuki,Okimoto, Mitsuhiro,Nakamura, Shingo,Takahashi, Shinya
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p. 3839 - 3847
(2012/01/04)
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- Synthesis of bis(alk-3-en-1-ynyl)benzene with either E- or Z-configuration via a one-pot three-component coupling reaction and its optical properties
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A convenient, efficient and stereoselective synthesis of a range of bis(alk-3-en-1-ynyl)benzenes with E- and Z-configuration is described. The protocol involves Cu-mediated cross-coupling reaction of (E)- and (Z)-alk-1-enyldisiamylboranes with (trimethyls
- Hoshi, Masayuki,Suzuki, Souichi,Saitoh, Shingo,Okimoto, Mitsuhiro,Shirakawa, Kazuya
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p. 119 - 124
(2007/10/03)
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- Construction of terminal conjugated enynes: Cu-mediated cross-coupling reaction of alkenyldialkylborane with (trimethylsilyl)ethynyl bromide
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The cross-coupling reaction of (E)- and (Z)-alk-1-enyldialkylborane with (trimethylsilyl)ethynyl bromide proceeds in the presence of a catalytic amount of copper(II) acetylacetonate and a base under extremely mild conditions to provide conjugated enynes w
- Hoshi, Masayuki,Kawamura, Noritsugu,Shirakawa, Kazuya
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p. 1961 - 1970
(2007/10/03)
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- Stereoselective syntheses of (E)- and (Z)-1-arylalk-3-en-1-ynes and (E,E)-, (Z,E)-, (E,Z)-, and (Z,Z)-alka-1,5-dien-3-ynes via a one-pot multicomponent coupling reaction
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Both 1-arylalk-3-en-1-ynes and alka-1,5-dien-3-ynes have been synthesized under extremely mild reaction conditions in good to high yields via a sequential Suzuki-type and Sonogashira reaction in a one-pot manner. Thus, the protocol involves Cu-mediated cross-coupling reaction of (E)- or (Z)- alkenyldisiamylborane with (trimethylsilyl)ethynyl bromide in the presence of 1M NaOMe and Pd/Cu-catalyzed cross-coupling reaction with aryl or alkenyl iodide in the presence of aqueous n-Bu4NOH. The reaction with aryl iodide is tolerant of a wide variety of functional groups on the aromatic ring and leads to the stereoselective formation of (E)- and (Z)-1-arylalk-3-en-1-ynes. In addition, the reactions with (E)- and (Z)-1-iodoalk-1-enes have accomplished the construction of all possible combinations of geometrical isomers, (E,E)-, (Z,E)-, (E,Z)-, and (Z,Z)-alka-1,5-dien-3-ynes. Georg Thieme Verlag Stuttgart.
- Hoshi, Masayuki,Nakayabu, Hidenori,Shirakawa, Kazuya
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p. 1991 - 2007
(2007/10/03)
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- Stereoselective dehalogenation of (Z)-1-halo-1-alkenyldialkylborane with tributyltin hydride: The behavior of tributyltin hydride as a hydride donor
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The reaction of (Z)-1-halo-1-alkenyldialkylborane (1) with tributyltin hydride (n-Bu3SnH) at 0°C or room temperature results in reductive removal of the halogen atom to afford (E)- or (Z)-1-alkenyldialkylborane whose stereochemistry depends on the dialkylboryl group and the alkenyl group of 1.
- Hoshi, Masayuki,Takahata, Kimitomo,Arase, Akira
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p. 453 - 456
(2007/10/03)
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