Heterocyclic compounds can be divided into two categories: alicyclic heterocycles and aromatic heterocycles. Compounds whose heterocycles in the molecular skeleton cannot reflect aromaticity are called alicyclic heterocyclic compounds. Compound: 1086138-36-4, is researched, Molecular C44H69NP2, about Erbium-Catalyzed Regioselective Isomerization-Cobalt-Catalyzed Transfer Hydrogenation Sequence for the Synthesis of Anti-Markovnikov Alcohols from Epoxides under Mild Conditions, the main research direction is tandem erbium catalyst regioselective isomerization cobalt transfer hydrogenation epoxide; synthesis anti Markovnikov alc.Synthetic Route of C44H69NP2.
Herein, we report an efficient isomerization-transfer hydrogenation reaction sequence based on a cobalt pincer catalyst (1 mol%), which allows the synthesis of a series of anti-Markovnikov alcs. from terminal and internal epoxides under mild reaction conditions (≤55°, 8 h) at low catalyst loading. The reaction proceeds by Lewis acid (3 mol % Er(OTf)3)-catalyzed epoxide isomerization and subsequent cobalt-catalyzed transfer hydrogenation using ammonia borane as the hydrogen source. The general applicability of this methodol. is highlighted by the synthesis of 43 alcs. from epoxides. A variety of terminal (23 examples) and 1,2-disubstituted internal epoxides (14 examples) bearing different functional groups are converted to the desired anti-Markovnikov alcs. in excellent selectivity and yields of up to 98%. For selected examples, it is shown that the reaction can be performed on a preparative scale up to 50 mmol. Notably, the isomerization step proceeds via the most stable carbocation. Thus, the regiochem. is controlled by stereoelectronic effects. As a result, in some cases, rearrangement of the carbon framework is observed when tri- and tetra-substituted epoxides (6 examples) are converted. A variety of functional groups are tolerated under the reaction conditions even though aldehydes and ketones are also reduced to the resp. alcs. under the reaction conditions. Mechanistic studies and control experiments were used to investigate the role of the Lewis acid in the reaction. Besides acting as the catalyst for the epoxide isomerization, the Lewis acid was found to facilitate the dehydrogenation of the hydrogen donor, which enhances the rate of the transfer hydrogenation step. These experiments addnl. indicate the direct transfer of hydrogen from the amine borane in the reduction step.
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Reference:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem