金（I）催化1-芳香基-2-(3-芳香基丙炔基)環己-2-烯-1-醇的分子內環化反應：四氫苯并[b]呋喃衍生物的合成
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2014
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Abstract
本文探討以氯化三苯基膦金 ( Ph3PAuCl ) 和三氟甲磺酸銀 ( AgOTf ) 共催化2號位帶炔基支鏈的六員環三級烯醇化合物進行分子內環化反應。
1-芳香基-2-(3-芳香基丙炔基)環己-2-烯-1-醇與催化量的氯化三苯基膦金和三氟甲磺酸銀，在氮氣、室溫的條件下，行分子內環化反應，數分鐘內即可得四氫苯并[b]呋喃衍生物。
此反應亦可應用在三級醇上帶長鏈烷基及長鏈炔基質，得到一系列在2號位或4號位具不同烴取代的四氫苯并[b]呋喃衍生物。
The thesis discusses chloro(triphenylphosphine)gold(I) (Ph3PAuCl) and silver trifluoromethanesulfonate (AgOTf) cocatalyzed intramolecular cycloisomerization of 1-arylcyclohex-2-en-1-ols bearing an alkynylalkyl tether at the C-2 position of the ring. Treatment of 1-aryl-2-(3-arylpropargyl)cyclohex-2-en-1-ols with a catalytic amount of Ph3PAuCl/AgOTf at room temperature under nitrogen in minutes provided tetrahydrobenzo[b]furan derivatives in good yields. This reaction can be expanded to an alkyl substitution at the tertiary carbinol carbon and the terminal alkyne, leading to 2 or 4-alkylsubstituted tetrahydrobenzo[b]furan derivatives.
The thesis discusses chloro(triphenylphosphine)gold(I) (Ph3PAuCl) and silver trifluoromethanesulfonate (AgOTf) cocatalyzed intramolecular cycloisomerization of 1-arylcyclohex-2-en-1-ols bearing an alkynylalkyl tether at the C-2 position of the ring. Treatment of 1-aryl-2-(3-arylpropargyl)cyclohex-2-en-1-ols with a catalytic amount of Ph3PAuCl/AgOTf at room temperature under nitrogen in minutes provided tetrahydrobenzo[b]furan derivatives in good yields. This reaction can be expanded to an alkyl substitution at the tertiary carbinol carbon and the terminal alkyne, leading to 2 or 4-alkylsubstituted tetrahydrobenzo[b]furan derivatives.
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苯并[b]呋喃, 金催化, 雜環, 三級醇, benzo[b]furan, gold catalyzed, heterocycle, tertiary alcohol