Organocatalytic γ′[C(sp3)-H] Functionalization of Ynones: An Unusual Approach for the Cyclopentannulation of Benzothiophenes

被引：9
作者：
Grover, Jagdeep [1 ]
Raghu, Moluguri [1 ]
Hazra, Raju [1 ]
Mondal, Atanu [1 ]
Ramasastry, S. S. V. [1 ]
机构：
[1] Indian Inst Sci Educ & Res IISER Mohali, Organ Synth & Catalysis Lab, Dept Chem Sci, Sect 81, Manauli Po 140306, Punjab, India
来源：
SYNTHESIS-STUTTGART | 2018年 / 50卷 / 07期
关键词：
organophosphines; hydroalkylation; cyclopentannulation; ynones; benzothiophenes; H BOND ACTIVATION; HETEROCYCLIC ORTHO-QUINODIMETHANES; TOMITA ZIPPER CYCLIZATION; CATALYZED 4+2 ANNULATION; BAYLIS-HILLMAN REACTION; DIELS-ALDER REACTIONS; ONE-POT SYNTHESIS; C-H; STEREOSELECTIVE-SYNTHESIS; TRIENAMINE CATALYSIS;
D O I：
10.1055/s-0036-1591526
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient organocatalytic approach for the cyclopenta[b]annulation of benzothiophenes via gamma'[C(sp3)-H] functionalization of ynones is described. Nucleophilic addition of an organophosphine to the designed ynones generates heteroaryl-based ortho-quinodimethanes (oQDMs), which undergo carbocyclization to provide a variety of cyclopenta-fused benzothiophenes. This approach also constitutes an unusual organophosphine-catalyzed intramolecular hydroalkylation of ynones.
引用
收藏
页码：1462 / 1470
页数：9
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