α-Arylation of Saturated Azacycles and N-Methylamines via Palladium(II)-Catalyzed C(sp3)-H Coupling

被引：141

作者：

Spangler, Jillian E. ^{[1
]}

Kobayashi, Yoshihisa ^{[2
]}

Verma, Pritha ^{[1
]}

Wang, Dong-Hui ^{[1
]}

Yu, Jin-Quan ^{[1
]}

机构：

[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA

[2] Eisai & Co Ltd, Med Chem, Eisai Product Creat Syst, Tsukuba, Ibaraki 3002635, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2015年 / 137卷 / 37期

关键词：

C-H BOND; CATALYZED HYDROAMINOALKYLATION; REDUCTIVE ELIMINATION; PHOTOREDOX CATALYSIS; UNACTIVATED OLEFINS; TANTALUM COMPLEXES; ALIPHATIC-AMINES; BOC-PYRROLIDINE; LITHIO AMINES; PALLADIUM;

D O I：

10.1021/jacs.5b06740

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Pd(II)-catalyzed alpha-C(sp(3))-H arylation of pyrrolidines, piperidines, azepanes, and N-methylamines with arylboronic acids has been developed for the first time. This transformation is applicable to wide arrays of pyrrolidines and boronic acids, including heteroaromatic boronic acids. A diastereoselective one-pot heterodiarylation of pyrrolidines has also been achieved.

引用

页码：11876 / 11879

页数：4

共 66 条

[1] Enantioselective, Palladium-Catalyzed α-Arylation of N-Boc Pyrrolidine: In Situ React IR Spectroscopic Monitoring, Scope, and Synthetic Applications
Barker, Graeme
McGrath, Julia L.
Klapars, Artis
Stead, Darren
Zhou, George
Campos, Kevin R.
O'Brien, Peter
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (15) : 5936 - 5953
[2] Diamine-Free Lithiation-Trapping of N-Boc Heterocycles using s-BuLi in THF
Barker, Graeme
O'Brien, Peter
Campos, Kevin R.
[J]. ORGANIC LETTERS, 2010, 12 (18) : 4176 - 4179
[3] Copper-catalyzed oxidative sp3 C-H bond arylation with aryl boronic acids
Basle, Olivier
Li, Chao-Jun
[J]. ORGANIC LETTERS, 2008, 10 (17) : 3661 - 3663
[4] Transition metal-catalyzed arylation of unactivated C(sp3)-H bonds
Baudoin, Olivier
[J]. CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) : 4902 - 4911
[5] COMPLEX-INDUCED PROXIMITY EFFECTS - ENANTIOSELECTIVE SYNTHESES BASED ON ASYMMETRIC DEPROTONATIONS OF N-BOC-PYRROLIDINES
BEAK, P
KERRICK, ST
WU, SD
CHU, JX
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (08) : 3231 - 3239
[6] Amine Functionalization via Oxidative Photoredox Catalysis: Methodology Development and Complex Molecule Synthesis
Beatty, Joel W.
Stephenson, Corey R. J.
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 2015, 48 (05) : 1474 - 1484
[7] Application of Catalytic Dynamic Resolution of N-Boc-2-lithiopiperidine to the Asymmetric Synthesis of 2-Aryl and 2-Vinyl Piperidines
Beng, Timothy K.
Gawley, Robert E.
[J]. ORGANIC LETTERS, 2011, 13 (03) : 394 - 397
[8] The Role of the Alcohol and Carboxylic Acid in Directed Ruthenium-Catalyzed C(sp3)-H α-Alkylation of Cyclic Amines
Bergman, Sheba D.
Storr, Thomas E.
Prokopcova, Hana
Aelvoet, Karel
Diels, Gaston
Meerpoel, Lieven
Maes, Bert U. W.
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (33) : 10393 - 10398
[9] Direct sp3 C-H bond activation adjacent to nitrogen in heterocycles
Campos, Kevin R.
[J]. CHEMICAL SOCIETY REVIEWS, 2007, 36 (07) : 1069 - 1084
[10] 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

← 1 2 3 4 5 6 7 →