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β-Amino Phosphine Mn Catalysts for 1,4-Transfer Hydrogenation of Chalcones and Allylic Alcohol Isomerization
Organometallics ( IF 2.5 ) Pub Date : 2019-11-05 , DOI: 10.1021/acs.organomet.9b00692 Vipulan Vigneswaran 1 , Samantha N. MacMillan 2 , David C. Lacy 1
Organometallics ( IF 2.5 ) Pub Date : 2019-11-05 , DOI: 10.1021/acs.organomet.9b00692 Vipulan Vigneswaran 1 , Samantha N. MacMillan 2 , David C. Lacy 1
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Mn complexes with amino acid derived PN ligands were used in the catalytic transfer hydrogenation (TH) of ketone and chalcone substrates in 2-propanol with mild heating. Moreover, chalcones are reduced selectively to the saturated ketone at short times and can be fully converted to the alcohol when reactions are prolonged. The mechanism of chalcone reduction was briefly considered. Allylic alcohols are not reactive in 2-propanol, but quantitative isomerization occurs in toluene. Thus, we suspect that the allylic alcohols are dehydrogenated and the resulting ketone is formed through a direct 1,4-hydrogenation of the chalcone. Finally, several other related ligands that have been used in Mn-based TH reactions were explored to test the viability of ligand design in favoring chemoselectivity. The β-amino phosphine ligands proved most effective in this regard.
中文翻译：
β-氨基膦锰催化剂用于Ch的1,4-转移加氢和烯丙醇异构化
带有氨基酸衍生的PN配体的Mn配合物用于酮和查尔酮底物在2-丙醇中温和加热的催化转移氢化（TH）。而且，查耳酮在短时间内选择性地还原成饱和酮，并且在反应延长时可以完全转化为醇。查尔酮减少的机制进行了简要考虑。烯丙醇在2-丙醇中不具有反应性，但是在甲苯中发生定量异构化。因此，我们怀疑烯丙基醇被脱氢，并且通过查耳酮的直接1，4-氢化形成了生成的酮。最后，探索了已在基于Mn的TH反应中使用的其他几种相关配体，以测试配体设计在促进化学选择性方面的可行性。
更新日期：2019-11-05
中文翻译：
β-氨基膦锰催化剂用于Ch的1,4-转移加氢和烯丙醇异构化
带有氨基酸衍生的PN配体的Mn配合物用于酮和查尔酮底物在2-丙醇中温和加热的催化转移氢化（TH）。而且，查耳酮在短时间内选择性地还原成饱和酮，并且在反应延长时可以完全转化为醇。查尔酮减少的机制进行了简要考虑。烯丙醇在2-丙醇中不具有反应性，但是在甲苯中发生定量异构化。因此，我们怀疑烯丙基醇被脱氢，并且通过查耳酮的直接1，4-氢化形成了生成的酮。最后，探索了已在基于Mn的TH反应中使用的其他几种相关配体，以测试配体设计在促进化学选择性方面的可行性。
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