A Solvent-Induced Reversal of Regioselectivity in the Suzuki Coupling of Pyrrole Esters

Yanan Zhang; Scott T. Handy

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A Solvent-Induced Reversal of Regioselectivity in the Suzuki Coupling of Pyrrole Esters

机译：吡咯酯的铃木偶联中溶剂诱导的区域选择性逆转

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During a study of the regioselectivity of the Suzuki coupling of dihalopyrrole esters, the first instance of a reversalof regioselectivity based upon a change in reaction solvent has been observed. It is believed that this change in regioselectivityis due to a change in solvation of the pyrrole ester, since a change in chemical shift values is observed forthe C3 and C5 protons upon going from DMF to chloroform to 3:1 benzene/methanol. An attempted application of thisregioselectivity to the synthesis of the lamellarin family of natural products is reported as well.

机译：在研究二卤代吡咯酯的Suzuki偶联的区域选择性时，已经观察到基于反应溶剂的改变而逆转区域选择性的第一种情况。据信，这种区域选择性的变化是由于吡咯酯的溶剂化的变化，因为从DMF到氯仿到3∶1的苯/甲醇时，观察到C 3和C 5质子的化学位移值发生了变化。还报道了这种区域选择性在天然产物lamellarin家族的合成中的尝试应用。

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《The Open Organic Chemistry Journal》 |2008年第1期|共7页
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Yanan Zhang; Scott T. Handy;
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中图分类有机化学;
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专利

1. Regioselective Suzuki cross-coupling reactions at the 2-position of Di- and tribrominated pyrroles [J] . Schroter S, Bach T Synlett . 2005,第12期

机译：在二溴和三溴吡咯的2位上的区域选择性Suzuki交叉偶联反应
2. Regioselective Suzuki cross-coupling reactions at the 2-position of Di- and tribrominated pyrroles [J] . Schroter S, Bach T Synlett . 2005,第12期

机译：在二溴和三溴吡咯的2位上的区域选择性Suzuki交叉偶联反应
3. Regioselective Bipyrrole Coupling of Pyrroles and 3-Substituted Pyrroles Using Phenyliodine(III) Bis(trifluoroacetate) [J] . Toshifumi Dohi, Koji Morimoto, Motoki Ito, Synthesis: International Journal of Methods in Synthetic Organic Chemistry . 2007,第18期

机译：使用苯基碘（III）双（三氟乙酸盐）的吡咯和3取代的吡咯的区域选择性联吡咯偶联
4. Copper–Bipyridine-Catalyzed Stereospecific Intramolecular Suzuki–Miyaura Coupling of α-Aminoalkylboronic Esters [C] . Yukako Yoshinaga, Takeshi Yamamoto, Michinori Suginome 日本化学会春季年会講演予稿集 . 2018

机译：α-氨基烷基硼酸酯的铜 - Bi0赖氨酸催化立体分子分子内铃木 - Miyaura偶联
5. Enantiospecific, regioselective Suzuki-Miyaura cross-couplings of secondary, allylic boronic esters. [D] . LaBine, Emily Judith. 2014

机译：对映体，区域选择性的仲烯丙基硼酸酯的Suzuki-Miyaura交叉偶联。
6. An Efficient Synthesis of Aryl-Substituted Pyrroles by the Suzuki–Miyaura Coupling Reaction of SEM-Protected Pyrroles [O] . Keli Cui, Meng Gao, Hongyi Zhao, 2019

机译：SEM保护的吡咯的Suzuki-Miyaura偶联反应可高效合成芳基取代的吡咯
7. A Solvent-Induced Reversal of Regioselectivity in the Suzuki Coupling of Pyrrole Esters [O] . Yanan Zhang, Scott T. Handy 2008

机译：吡咯酯铃木偶联中的溶剂诱导的逆向逆转

A Solvent-Induced Reversal of Regioselectivity in the Suzuki Coupling of Pyrrole Esters

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