Fe-catalyzed Decarbonylative Alkylative Spirocyclization of N-Arylcinnamamides: Access to Alkylated 1-Azaspirocyclohexadienones

Xiang Peng; Ren-Xiang Liu; Xiang-Yan Xiao; Luo Yang

doi:10.3390/molecules25030432

Fe-catalyzed Decarbonylative Alkylative Spirocyclization of N-Arylcinnamamides: Access to Alkylated 1-Azaspirocyclohexadienones

Molecules ◽

10.3390/molecules25030432 ◽

2020 ◽

Vol 25 (3) ◽

pp. 432

Author(s):

Xiang Peng ◽

Ren-Xiang Liu ◽

Xiang-Yan Xiao ◽

Luo Yang

Keyword(s):

Radical Addition ◽

Aliphatic Aldehydes ◽

Alkyl Radicals ◽

Alkyl Groups ◽

Tertiary Alkyl

For the convenient introduction of simple linear/branched alkyl groups into biologically important azaspirocyclohexadienones, a practical Fe-catalyzed decarbonylative cascade spiro-cyclization of N-aryl cinnamamides with aliphatic aldehydes to provide alkylated 1-azaspiro-cyclohexadienones was developed. Aliphatic aldehydes were oxidative decarbonylated into primary, secondary and tertiary alkyl radicals conveniently and allows for the subsequent cascade construction of dual C(sp3)-C(sp3) and C=O bonds via radical addition, spirocyclization and oxidation sequence.

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Co-Catalyzed decarbonylative alkylative esterification of styrenes with aliphatic aldehydes and hypervalent iodine(iii) reagents

Organic Chemistry Frontiers ◽

10.1039/c9qo00748b ◽

2019 ◽

Vol 6 (17) ◽

pp. 3065-3070 ◽

Cited By ~ 3

Author(s):

Yong Peng ◽

Yuan-Yuan Jiang ◽

Xue-Jiao Du ◽

Da-You Ma ◽

Luo Yang

Keyword(s):

Radical Addition ◽

Hypervalent Iodine ◽

Aliphatic Aldehydes ◽

Alkyl Radicals

Decarbonylation of aliphatic aldehydes into 1°, 2° and 3° alkyl radicals to construct C(sp3)–C(sp3) bond via radical addition and C(sp3)–O bond via the interconversion of CoII–CoIII–CoI.

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Facile transfer of tertiary alkyl groups from boron to carbon in the base-induced reaction of .alpha.,.alpha.-dichloromethyl methyl ether with organoboranes containing tertiary alkyl groups. Novel route to highly hindered trialkylcarbinols involving exceptionally mild conditions

The Journal of Organic Chemistry ◽

10.1021/jo00962a041 ◽

1973 ◽

Vol 38 (22) ◽

pp. 3968-3970 ◽

Cited By ~ 32

Author(s):

Herbert C. Brown ◽

Jean Jacques Katz ◽

Bruce A. Carlson

Keyword(s):

Methyl Ether ◽

Mild Conditions ◽

Alkyl Groups ◽

Tertiary Alkyl ◽

Induced Reaction

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Electron affinities of a homologous series of tertiary alkyl radicals and their C–H bond dissociation energies (BDEs)

Tetrahedron ◽

10.1016/j.tet.2008.12.043 ◽

2009 ◽

Vol 65 (8) ◽

pp. 1655-1659 ◽

Cited By ~ 2

Author(s):

Panayiotis S. Petrou ◽

Athanassios V. Nicolaides

Keyword(s):

Homologous Series ◽

Bond Dissociation Energies ◽

Electron Affinities ◽

Alkyl Radicals ◽

Bond Dissociation ◽

Dissociation Energies ◽

Tertiary Alkyl

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Introduction of Tertiary Alkyl Groups into CH-Acidic Compounds

Angewandte Chemie International Edition in English ◽

10.1002/anie.196610443 ◽

1966 ◽

Vol 5 (12) ◽

pp. 1044-1045 ◽

Cited By ~ 2

Author(s):

P. Boldt ◽

W. Thielecke

Keyword(s):

Alkyl Groups ◽

Acidic Compounds ◽

Tertiary Alkyl

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Radical Addition of Hydroxy Quinazolines and Alkylation of Quinones via the Electro-induced Homolysis of 4-Alkyl-1,4-dihydropyridines

Synthesis ◽

10.1055/a-1737-2765 ◽

2022 ◽

Author(s):

Xiaosheng Luo ◽

Qiping Feng ◽

Ping Wang

Keyword(s):

Radical Addition ◽

Alkyl Radicals ◽

Mild Conditions

Herein, we report the formation of C(sp3)-centered radicals via the electro-induced homolysis of 4-alkyl-1,4-dihydropyridines (alkyl-DHPs). The resulting alkyl radicals reacted with hydroxy quinazolines or quinones to afford 2-alkyl dihydroquinazolinones or alkylated quinones. A broad range of alkyl DHPs could be used as versatile radical precursors under electrolysis conditions. This alterative strategy provided a simple and effective pathway for the construction of C(sp2)–C(sp3) and C(sp3)–C(sp3) bonds under mild conditions.

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Copper-catalyzed direct alkylation of heteroarenes

Chemical Science ◽

10.1039/c6sc05622a ◽

2017 ◽

Vol 8 (5) ◽

pp. 3465-3470 ◽

Cited By ~ 38

Author(s):

Cédric Theunissen ◽

Jianjun Wang ◽

Gwilherm Evano

Keyword(s):

Alkyl Radicals ◽

Alkyl Bromides ◽

Tertiary Alkyl

An efficient and broadly applicable process is reported for the direct alkylation of heteroarene C–H bonds, based on the copper-catalyzed addition of alkyl radicals generated from activated secondary and tertiary alkyl bromides to a range of arenes, and their benzo-fused derivatives.

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