Radical-radical cross coupling reactions of photo-excited fluorenones

被引：17

作者：

Sharma, Simmi ^{[1
]}

Sultan, Shaista ^{[1
]}

Devari, Shekaraiah ^{[1
]}

Shah, Bhahwal Ali ^{[1
]}

机构：

[1] Indian Inst Integrat Med, CSIR, Nat Prod Microbes, Acad Sci & Innovat Res, Canal Rd, Jammu 180001, India

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2016年 / 14卷 / 40期

关键词：

SINGLE-ELECTRON-TRANSFER; DYNAMIC KINETIC RESOLUTION; CATALYZED DEHYDROGENATIVE CYCLIZATION; AROMATIC CARBONYL-COMPOUNDS; C-H FUNCTIONALIZATION; ALPHA-AMINO RADICALS; VISIBLE-LIGHT; CARBOXYLIC-ACIDS; ENANTIOSELECTIVE SYNTHESIS; MERGING PHOTOREDOX;

D O I：

10.1039/c6ob01879c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Radical-radical cross coupling reactions of photoexcited 9-fluorenones have been accomplished for the first time, leading to the synthesis of 9-alkyl, pyrollidinyl and spiro-THF derivatives of 9-fluorenones. The method also reveals, for the first time, the behaviour of ketyl radicals in decarboxyaltive alkylation and ring expansion reactions.

引用

页码：9645 / 9649

页数：5

共 74 条

[1] A Chiral Metal Photocatalyst Architecture for Highly Enantioselective Photoreactions [J].

Amador, Adrian G. ;

Yoon, Tehshik P. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (07) :2304-2306

[2] CYCLIC HEMIAMINAL FORMATION IN SOME N-UNSUBSTITUTED AZOLE ALDEHYDES [J].

BROWNE, EJ .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1971, 24 (11) :2389-&

[3] THE COMBINATORIAL SYNTHESIS AND CHEMICAL AND BIOLOGICAL EVALUATION OF A 1,4-BENZODIAZEPINE LIBRARY [J].

BUNIN, BA ;

PLUNKETT, MJ ;

ELLMAN, JA .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1994, 91 (11) :4708-4712

[4] A direct and versatile access to α,α-disubstituted 2-pyrrolidinylmethanols by Sml2-mediated reductive coupling [J].

Burchak, Olga N. ;

Philouze, Christian ;

Chavant, Pierre Yves ;

Py, Sandrine .

ORGANIC LETTERS, 2008, 10 (14) :3021-3023

[5] THE 9-FLUORENYLMETHYLOXYCARBONYL FAMILY OF BASE-SENSITIVE AMINO-PROTECTING GROUPS [J].

CARPINO, LA .

ACCOUNTS OF CHEMICAL RESEARCH, 1987, 20 (11) :401-407

[6] Cytochrome P450-catalyzed oxidation of N-benzyl-N-cyclopropylamine generates both cyclopropanone hydrate and 3-hydroxypropionaldehyde via hydrogen abstraction, not single electron transfer [J].

Cerny, MA ;

Hanzlik, RP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (10) :3346-3354

[7] An unusual chemoselective oxidation strategy by an unprecedented exploration of an electrophilic center of DMSO: a new facet to classical DMSO oxidation [J].

Chebolu, Rajesh ;

Bahuguna, Ashish ;

Sharma, Reena ;

Mishra, Vivek Kumar ;

Ravikumar, P. C. .

CHEMICAL COMMUNICATIONS, 2015, 51 (84) :15438-15441

[8] Studies Leading to the Development of a Single-Electron Transfer (SET) Photochemical Strategy for Syntheses of Macrocyclic Polyethers, Polythioethers, and Polyamides [J].

Cho, Dae Won ;

Yoon, Ung Chan ;

Mariano, Patrick S. .

ACCOUNTS OF CHEMICAL RESEARCH, 2011, 44 (03) :204-215

[9] Metal free access to quinolines via C-C bond cleavage of styrenes [J].

Deshidi, Ramesh ;

Devari, Shekaraiah ;

Shah, Bhahwal Ali .

ORGANIC CHEMISTRY FRONTIERS, 2015, 2 (05) :515-519

[10] Iodine-Promoted Oxidative Amidation of Terminal Alkenes - Synthesis of α-Ketoamides, Benzothiazoles, and Quinazolines [J].

Deshidi, Ramesh ;

Devari, Shekaraiah ;

Shah, Bhahwal Ali .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (07) :1428-1432

← 1 2 3 4 5 6 7 8 →