Gold-Catalyzed One-Pot A3-Coupling/1,5-Hydride Shift/Schmittel-Type Cyclization: From Aldehydes, Amines and Alkynes to the Synthesis of Benzo[b]fluorenes

被引：13

作者：

Lustosa, Danilo M. ^{[1
]}

Hartmann, Deborah ^{[1
]}

Rudolph, Matthias ^{[1
]}

Rominger, Frank ^{[1
]}

Hashmi, A. Stephen K. ^{[1
,2
]}

机构：

[1] Heidelberg Univ, Organ Chem Inst, Neuenheimer Feld 270, D-69120 Heidelberg, Germany

[2] King Abdulaziz Univ, Fac Sci, Chem Dept, Jeddah 21589, Saudi Arabia

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 2020卷 / 09期

关键词：

Benzo[b]fluorenes; Allenes; Cascade reaction; Gold; Schmittel cyclization; HIGHLY ENANTIOSELECTIVE SYNTHESIS; ENYNE-ALLENES; EFFICIENT SYNTHESIS; CHIRALITY TRANSFER; MYERS-SAITO; C BOND; DERIVATIVES; CORE; KINAMYCINS; CARBONATES;

D O I：

10.1002/ejoc.201901906

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A step-economic gold-catalyzed one-pot synthesis of benzo[b]fluorenes, from aldehydes, alkynes and amines, proceeding via an A(3)-coupling/1,5-hydride shift/Schmittel-type cyclization is described. The formation of the allene intermediate is not dependent on a previous installation of reaction triggers, and upon cyclization delivered benzo[b]fluorenes. With this method, just by an easy modification of the starting materials in a modular way, nineteen benzo[b]fluorenes, bearing different substituents Ar-1, Ar-2 and Ar-3, were prepared. Overall, three new carbon-carbon bonds are formed in one-pot.

引用

页码：1160 / 1164

页数：5

共 7 条

[1] Gold-Catalyzed One-Pot Synthesis of 1,3-Disubstituted Allenes from Benzaldehydes and Terminal Alkynes
Lustosa, Danilo M.
Clemens, Simon
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Hashmi, A. Stephen K.
ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (21) : 5050 - 5056
[2] CuI-nanoparticles-catalyzed one-pot synthesis of benzo[b]furans via three-component coupling of aldehydes, amines and alkyne
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[3] PTSA-catalyzed Mannich-type-cyclization-oxidation tandem reactions: one-pot synthesis of 1,3,5-substituted pyrazoles from aldehydes, hydrazines and alkynes
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Pan, Ying-Ming
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[4] Gold(I)-Catalyzed One-Pot Tandem Coupling/Cyclization: An Efficient Synthesis of Pyrrolo-/Pyrido[2,1-b]benzo[d][1,3]oxazin-1-ones
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[5] Pd-Catalyzed One-Pot Stepwise Synthesis of Benzo[b][1,6]naphthyridines from 2-Chloroquinoline-3-carbonitriles Using Sulfur and Amines As Nucleophiles
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[6] Altering Copper-Catalyzed A3 Couplings by Mechanochemistry: One-Pot Synthesis of 1,4-Diamino-2-butynes from Aldehydes, Amines, and Calcium Carbide
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[7] Synthesis of (Z)-1,2-dihydro-1-tosylbenzo[b]azepin-3-ones by two-step, one-pot gold-catalyzed tandem heterocyclization/Petasis-Ferrier rearrangement of 2-(N-(prop-2-ynyl)-N-tosylamino)benzaldehydes
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