A Versatile C-H Functionalization of Tetrahydroisoquinolines Catalyzed by Iodine at Aerobic Conditions

被引：250

作者：

Dhineshkumar, Jayaraman ^{[1
]}

Lamani, Manjunath ^{[1
]}

Alagiri, Kaliyamoorthy ^{[1
]}

Prabhu, Kandikere Ramaiah ^{[1
]}

机构：

[1] Indian Inst Sci, Dept Organ Chem, Bangalore 560012, Karnataka, India

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 05期

关键词：

DEHYDROGENATIVE COUPLING REACTIONS; TERTIARY-AMINES; MOLECULAR-OXYGEN; OXIDATIVE CYANATION; HYDROGEN-PEROXIDE; BOND FORMATION; ACTIVATION; AMINATION; HETEROCYCLES; CDC;

D O I：

10.1021/ol4001153

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A versatile aerobic catalytic system (I-2 and O-2/TBHP) for C-H functionalization is reported. This CDC (cross-dehydrogentive coupling) reaction is compatible with a large number of nucleophiles and is performed under ambient reaction conditions. The scope of the metal-free CDC is illustrated by synthesizing a variety of functionalized tetrahydroisoquinolines and N,N-dimethylaniline. The highlight of the method is a Friedel-Crafts reaction of phenols and indole with tertiary amines.

引用

页码：1092 / 1095

页数：4

共 67 条

[1] CDC Reactions of N-Aryl Tetrahydroisoquinolines Using Catalytic Amounts of DDQ: C-H Activation under Aerobic Conditions
Alagiri, Kaliyamoorthy
Devadig, Pradeep
Prabhu, Kandikere R.
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (17) : 5160 - 5164
[2] Molybdenum trioxide catalyzed oxidative cross-dehydrogenative coupling of benzylic sp3 C-H bonds: synthesis of α-aminophosphonates under aerobic conditions
Alagiri, Kaliyamoorthy
Devadig, Pradeep
Prabhu, Kandikere R.
[J]. TETRAHEDRON LETTERS, 2012, 53 (12) : 1456 - 1459
[3] C-H functionalization of tertiary amines by cross dehydrogenative coupling reactions: solvent-free synthesis of α-aminonitriles and β-nitroamines under aerobic condition
Alagiri, Kaliyamoorthy
Prabhu, Kandikere Ramaiah
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (04) : 835 - 842
[4] An oxidative cross-dehydrogenative-coupling reaction in water using molecular oxygen as the oxidant: vanadium catalyzed indolation of tetrahydroisoquinolines
Alagiri, Kaliyamoorthy
Siddappa, Guralamatta
Kumara, Ravi
Prabhu, Kandikere Ramaiah
[J]. CHEMICAL COMMUNICATIONS, 2011, 47 (42) : 11787 - 11789
[5] Tropylium Ion Mediated α-Cyanation of Amines
Allen, Julia M.
Lambert, Tristan H.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (05) : 1260 - 1262
[6] Arend M, 1998, ANGEW CHEM INT EDIT, V37, P1044, DOI 10.1002/(SICI)1521-3773(19980504)37:8<1044::AID-ANIE1044>3.0.CO
[7] 2-E
[8] Copper catalyzed oxidative alkylation of sp3 C-H bond adjacent to a nitrogen atom using molecular oxygen in water
Basle, Olivier
Li, Chao-Jun
[J]. GREEN CHEMISTRY, 2007, 9 (10) : 1047 - 1050
[9] Copper-catalyzed aerobic phosphonation of sp3 C-H bonds
Basle, Olivier
Li, Chao-Jun
[J]. CHEMICAL COMMUNICATIONS, 2009, (27) : 4124 - 4126
[10] A Comparative Mechanistic Study of Cu-Catalyzed Oxidative Coupling Reactions with N-Phenyltetrahydroisoquinoline
Boess, Esther
Schmitz, Corinna
Klussmann, Martin
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (11) : 5317 - 5325

← 1 2 3 4 5 6 7 →