Carbonate-assisted selectively deoxygenative cross-coupling reaction between aryl and aliphatic aldehydes: a straightforward route to access α-alkylated aryl ketones

被引:0
作者
Sun, Yu [1 ]
Wang, Yi [1 ]
Zuo, Zhijun [1 ]
机构
[1] Northwest Univ, Coll Chem & Mat Sci, Key Lab Synthet & Nat Funct Mol, Minist Educ, Xian 710127, Peoples R China
关键词
THIAZOLIUM SALT; ARYLATION; REDUCTION; OXIDATION; ALCOHOLS; BENZOIN; DEHYDROXYLATION; ORGANOCATALYSIS; CATALYSIS; REAGENTS;
D O I
10.1039/d4qo01517g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
alpha-Alkylated aryl ketones play a prominent role in pharmaceutically active compounds. Thus, developing a straightforward and atom/step-economical strategy for gaining modular access to these privileged structural motifs is of central importance. Herein, we describe a novel direct reductive cross-coupling reaction of aryl-aliphatic or aryl-aryl aldehydes. This reaction demonstrates a unique feature of merging two different aldehydes using inexpensive carbonate as a reductant with excellent chemoselectivities. This novel protocol has a broad substrate scope with excellent functional group tolerance, which allows one to prepare a library of valuable alpha-alkylated aryl ketones and bioactive molecules by late-stage functionalization. Moreover, a series of mechanistic studies uncovers a rational pathway for these transformations. A novel reductive cross-coupling reaction of two different aldehydes for rapidly assembling alpha-alkylated aryl ketones has been developed. The inexpensive carbonate served not only as a base but also as an efficient electron donor.
引用
收藏
页码:6510 / 6517
页数:8
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