Palladium-catalyzed, aminoquinoline-directed arylation of phosphonamidate and phosphinic amide sp3 C-H bonds

被引：15

作者：

Tung Thanh Nguyen ^{[1
]}

Daugulis, Olafs ^{[1
]}

机构：

[1] Univ Houston, Dept Chem, Univ Pk, Houston, TX 77204 USA

来源：

CHEMICAL COMMUNICATIONS | 2017年 / 53卷 / 33期

关键词：

CARBON-HYDROGEN BONDS; CYCLIZATION; ACTIVATION; FUNCTIONALIZATION; ALKYLATION; PHENOLS; OXIDES; SP(2); SCOPE;

D O I：

10.1039/c7cc02063e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Aminoquinoline-directed, palladium-catalyzed sp(3) C-H bond arylation in phosphonamidates and phosphinic amides is reported. The reaction employs Pd(OAc)(2) as a catalyst at 10 mol% loading and cesium phosphate or potassium carbonate as a base in 1,2-dichlorobenzene as a solvent. The directing group can be removed under basic conditions to afford phosphonic acid esters. The chemistry described here is the first example of unactivated sp(3) C-H bond arylation by using a phosphorus-containing directing group.

引用

页码：4609 / 4611

页数：3

共 50 条

[1] Cobalt-Catalyzed, Aminoquinoline-Directed Functionalization of Phosphinic Amide sp2 C-H Bonds
Tung Thanh Nguyen
Grigorjeva, Liene
Daugulis, Olafs
ACS CATALYSIS, 2016, 6 (02): : 551 - 554
[2] Palladium-Catalyzed Pyrazole-Directed sp3 C-H Bond Arylation for the Synthesis of β-Phenethylamines
Gulia, Nurbey
Daugulis, Olafs
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (13) : 3630 - 3634
[3] Palladium-Catalyzed Direct Arylation of C(sp3)-H Bonds of α-Cyano Aliphatic Amides
Reddy, M. Damoder
Watkins, E. Blake
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (22) : 11447 - 11459
[4] Cobalt-Catalyzed, Aminoquinoline-Directed Coupling of sp2 C-H Bonds with Alkenes
Grigorjeva, Liene
Daugulis, Olafs
ORGANIC LETTERS, 2014, 16 (17) : 4684 - 4687
[5] Palladium-Catalyzed Arylation of C(sp2)-H Bonds and C(sp3)-H Bonds with 4-Amino-benzotriazole as the Bidentate Directing Group
Li, Chengqian
Wang, Zhuo
Jin, Meina
Song, Zhiguang
JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (10) : 6966 - 6973
[6] Palladium-catalyzed acetoxylation of sp3 C-H bonds using molecular oxygen
Jiang, Huanfeng
Chen, Huoji
Wang, Azhong
Liu, Xiaohang
CHEMICAL COMMUNICATIONS, 2010, 46 (38) : 7259 - 7261
[7] Scope and Limitations of Auxiliary-Assisted, Palladium-Catalyzed Arylation and Alkylation of sp2 and sp3 C-H Bonds
Nadres, Enrico T.
Santos, Gerson Ivan Franco
Shabashov, Dmitry
Daugulis, Olafs
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (19) : 9689 - 9714
[8] A Simple Aliphatic Diamine Auxiliary for Palladium-Catalyzed Arylation of Unactivated β-C(sp3)-H Bonds
Lou, Jiang
Wang, Quannan
He, Yuan
Yu, Zhengkun
ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (23) : 4571 - 4584
[9] Amide-directed arylation of sp3 C-H bonds using Pd(II) and Pd(0) catalysts
Wasa, Masayuki
Yu, Jin-Quan
TETRAHEDRON, 2010, 66 (26) : 4811 - 4815
[10] Palladium-Catalyzed Secondary C(sp3)-H Arylation of 2-Alkylpyridines
Li, Hong-Liang
Kuninobu, Yoichiro
ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (13) : 2637 - 2641

← 1 2 3 4 5 →