Synthesis of 9,10-Diarylanthracenes via Mg(TMP)2_2LiCl-Mediated Benzyne Generation/[4+2] Cycloaddition and Deoxygenation of 9,10-Epoxyanthracene Intermediates
Synthesis of 9,10-Diarylanthracenes via Mg(TMP)2_2LiCl-Mediated Benzyne Generation/[4+2] Cycloaddition and Deoxygenation of 9,10-Epoxyanthracene Intermediates
复制标题
Mg(TMP)2_2LiCl介导的苯炔生成合成9,10-二芳基蒽/[4 2] 9,10-环氧蒽中间体的环加成和脱氧
作者：
Miyamoto;N.; Nakazawa;Y.; Nakamura;T.; Okano;K.; Sato;S.; Sun;Z.; Isobe;H.; Tokuyama;H.
提出了一条合成功能化9，10-二芳基蒽的新路线。通过Mg（TMP）2·2LiCl介导的苯炔生成反应，合成了1，3-二芳基异苯并呋喃与多种功能化苯炔中间体，通过[4+2]环加成反应合成了9，10-环氧蒽中间体。为了裂解所得9，10-环氧蒽中间体，我们开发了使用三氟乙酸和Et 3SiH组合的温和脱氧条件。通过应用于5，7，12，14-四苯基并五苯的合成，证明了该序列的实用性。
A new synthetic route to functionalized 9,10-diarylanthracenes has been developed. 9,10-Epoxyanthracene intermediates were prepared by [4+2] cycloaddition of 1,3-diarylisobenzofuran with a variety of functionalized benzyne intermediates, which were obtained by Mg(TMP)2·2LiCl-mediated benzyne generation. For the cleavage of the resultant 9,10-epoxyanthracene intermediates, we developed mild deoxygenation conditions using a combination of trifluoroacetic acid and Et3SiH. The utility of this sequence was demonstrated by application to the synthesis of 5,7,12,14-tetraphenylpentacene.