Boron-complexation strategy for use with 1-acyldipyrromethanes.
Boron-complexation strategy for use with 1-acyldipyrromethanes.
复制标题
与 1-酰基二吡咯甲烷一起使用的硼络合策略。
DOI：
10.1021/jo0492620
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发表时间：
2004
期刊：
影响因子：
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通讯作者：
Lindsey,JonathanS
中科院分区：
文献类型：
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作者：
Muthukumaran,Kannan;Ptaszek,Marcin;Noll,Bruce;Scheidt,WRobert;Lindsey,JonathanS
1-酰基二吡咯烷是合理合成多种卟啉类化合物的重要前体。1-酰基二吡啶甲烷很难纯化，通常在色谱上有条纹，在尝试结晶时产生无定形粉末。通过将1-酰基二吡咯甲烷与二烷基三氟化硼（如Bu2B-OTf或9-BBN-OTf）反应得到相应的b， b -二烷基- b -（1-酰基二吡咯甲烷）硼（III）配合物，可以解决这一问题。在二吡咯甲烷存在下，该反应对1-酰基二吡咯甲烷具有选择性。1-酰基二吡咯甲烷-硼配合物对常规处理稳定，可溶于常见的有机溶剂，疏水，易结晶，在色谱仪上无条纹。经1-戊醇处理后，硼配合物可高产出1-酰基二吡咯甲烷。另外，1-酰基二吡咯甲烷-硼配合物可用于生成attrans - a2b2 -卟啉。综上所述，硼络合策略适用范围广，极大地促进了1-酰基二吡咯烷的分离。
1-Acyldipyrromethanes are important precursors in rational syntheses of diverse porphyrinic compounds. 1-Acyldipyrromethanes are difficult to purify, typically streaking upon chromatography and giving amorphous powders upon attempted crystallization. A solution to this problem has been achieved by reacting the 1-acyldipyrromethane with a dialkylboron triflate (e.g., Bu2B-OTf or 9-BBN-OTf) to give the correspondingB,B-dialkyl-B-(1-acyldipyrromethane)boron(III) complex. The reaction is selective for a 1-acyldipyrromethane in the presence of a dipyrromethane. The 1-acyldipyrromethane−boron complexes are stable to routine handling, are soluble in common organic solvents, are hydrophobic, crystallize readily, and chromatograph without streaking. The 1-acyldipyrromethane can be liberated in high yield from the boron complex upon treatment with 1-pentanol. Alternatively, the 1-acyldipyrromethane−boron complex can be used in the formation of atrans-A2B2-porphyrin. In summary, the boron-complexation strategy has broad scope and greatly facilitates the isolation of 1-acyldipyrromethanes.