Borrowing hydrogen C-alkylation with secondary saturated heterocyclic alcohols

被引:1
作者
Francois, Jordan [1 ]
Jacolot, Maiwenn [1 ]
Popowycz, Florence [1 ]
机构
[1] Univ Lyon 1, CNRS, UMR 5246, CPE Lyon,ICBMS,INSA Lyon, 1 Rue Victor Grignard, F-69621 Villeurbanne, France
关键词
CATALYZED ALPHA-ALKYLATION; KETONES; DEHYDROGENATION; TETRAHYDROFURAN; ACTIVATION; PRODUCTS; IRIDIUM;
D O I
10.1039/d4ob00543k
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The borrowing hydrogen methodology (BH) has emerged as a powerful tool for the rapid construction of C-C bonds, offering a greener alternative to traditional multi-step syntheses. This methodology involves the activation of inactivated alcohols followed by condensation or aldolization, ultimately leading to the regeneration of the saturated product. Herein, we report the C-alkylation of a hindered ketone with challenging secondary saturated heterocyclic alcohols. Our study encompasses the optimization of reaction conditions using either an iridium or a ruthenium catalyst and exploration of substrate scope. We demonstrate the efficient synthesis of substituted pyrrolidines and piperidines directly from a triol precursor, showcasing the versatility of this methodology. Moreover, we illustrate the post-functionalization of BH products, significantly broadening their chemical utility.
引用
收藏
页码:4502 / 4507
页数:6
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