sp3 C-H bond arylation directed by amidine protecting group:: α-arylation of pyrrolidines and piperidines

被引：280

作者：

Pastine, Stefan J. ^{[1
]}

Gribkov, Denis V. ^{[1
]}

Sames, Dalibor ^{[1
]}

机构：

[1] Columbia Univ, Dept Chem, New York, NY 10027 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2006年 / 128卷 / 44期

关键词：

D O I：

10.1021/ja064481j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new ruthenium-catalyzed direct sp3 C-H to C-C bond transformation is disclosed. Specifically, a method for the α-arylation of cyclic amines, containing either permanent (pyridine, pyrimidine) or removable (amidine) directing groups, is described. This cross-coupling reaction involves heating amine substrates with arylboronate ester at 150 °C in a ketone solvent with a catalytic amount of ruthenium carbonyl [Ru3(CO)12]. Arylboronate esters containing either electron-withdrawing or electron-donating substituents could be efficiently coupled. Heteroarene boronates were also effective donors. Copyright © 2006 American Chemical Society.

引用

页码：14220 / 14221

页数：2

共 20 条

[1] DOUBLE C-H ACTIVATION AT THE ALPHA-CARBON OF CYCLIC ETHERS BY TP-ASTERISK-IR(C2H4)2
BOUTRY, O
GUTIERREZ, E
MONGE, A
NICASIO, MC
PEREZ, PJ
CARMONA, E
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (18) : 7288 - 7290
[2] Enantioselective, palladium-catalyzed α-arylation of N-Boc-pyrrolidine
Campos, KR
Klapars, A
Waldman, JH
Dormer, PG
Chen, CY
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (11) : 3538 - 3539
[3] Ru3(CO)12-catalyzed coupling reaction of sp3 C-H bonds adjacent to a nitrogen atom in alkylamines with alkenes
Chatani, N
Asaumi, T
Yorimitsu, S
Ikeda, T
Kakiuchi, F
Murai, S
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (44) : 10935 - 10941
[4] Carbonylation at sp3 C-H bonds adjacent to a nitrogen atom in alkylamines catalyzed by rhodium complexes
Chatani, N
Asaumi, T
Ikeda, T
Yorimitsu, S
Ishii, Y
Kakiuchi, F
Murai, S
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (51) : 12882 - 12883
[5] C-C bond formation via C-H bond activation: Synthesis of the core of teleocidin B4
Dangel, BD
Godula, K
Youn, SW
Sezen, B
Sames, D
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (40) : 11856 - 11857
[6] Cross-coupling of sp3 C-H bonds and alkenes:: Catalytic cyclization of alkene-amide substrates
DeBoef, B
Pastine, SJ
Sames, D
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (21) : 6556 - 6557
[7] Copper cyanide-catalyzed palladium coupling of N-tert-butoxycarbonyl-protected alpha-lithio amines with aryl iodides or vinyl iodides
Dieter, RK
Li, SJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (22) : 7726 - 7735
[8] Geminal dehydrogenation of ether and amine C(sp3)H2 groups by electron-rich Ru(II) and Os
Ferrando-Miguel, G
Coalter, JN
Gérard, H
Huffman, JC
Eisenstein, O
Caulton, KG
[J]. NEW JOURNAL OF CHEMISTRY, 2002, 26 (06) : 687 - 700
[9] C-H bond functionalization in complex organic synthesis
Godula, K
Sames, D
[J]. SCIENCE, 2006, 312 (5770) : 67 - 72
[10] Chelation-assisted alkylation of benzylamine derivatives by Ru0 catalyst
Jun, CH
Hwang, DC
Na, SJ
[J]. CHEMICAL COMMUNICATIONS, 1998, (13) : 1405 - 1406

← 1 2 →