BrettPhos Ligand Supported Palladium-Catalyzed C-O Bond Formation through an Electronic Pathway of Reductive Elimination: Fluoroalkoxylation of Activated Aryl Halides

被引：60

作者：

Rangarajan, T. M. ^{[1
,3
]}

Singh, Rajendra ^{[2
]}

Brahma, Raju ^{[2
]}

Devi, Kavita ^{[2
]}

Singh, Rishi Pal ^{[1
]}

Singh, R. P. ^{[2
]}

Prasad, Ashok K. ^{[3
]}

机构：

[1] Univ Delhi, Sri Venkateswara Coll, Dept Chem, New Delhi, India

[2] DRDO, Fluoroorgan Lab, Ctr Fire Explos & Environm Safety, Delhi, India

[3] Univ Delhi, Dept Chem, Delhi 110007, India

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2014年 / 20卷 / 44期

关键词：

alcohols; BrettPhos; CO coupling; ethers; reductive elimination; CROSS-COUPLING REACTIONS; ALPHA-FLUORINATED ETHERS; BETA-AMYLOID PLAQUES; DIARYL ETHERS; 2,2,2-TRIFLUOROETHYL ETHERS; AROMATIC FLUOROALKOXYLATION; AMINATION REACTIONS; EFFICIENT CATALYST; PHOSPHINE-LIGANDS; PRIMARY ALCOHOLS;

D O I：

10.1002/chem.201404121

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We report an unprecedented BrettPhos ligand supported Pd-catalyzed CO bond-forming reaction of activated aryl halides with primary fluoroalkyl alcohols. We demonstrate that the Phosphine ligand (BrettPhos) possesses the property of altering the mechanistic pathway of reductive elimination from nucleophile to nucleophile. The Pd/BrettPhos catalyst system facilitates the reductive elimination of the oxygen nucleophile through an electronic pathway.

引用

页码：14218 / 14225

页数：8

共 40 条

[1] Palladium-catalyzed C-O bond formation: direct synthesis of phenols and aryl/alkyl ethers from activated aryl halides
Chen, Guoshu
Chan, Albert S. C.
Kwong, Fuk Yee
TETRAHEDRON LETTERS, 2007, 48 (03) : 473 - 476
[2] Palladium-catalyzed C-O coupling involving unactivated aryl halides. Sterically induced reductive elimination to form the C-O bond in diaryl ethers
Mann, G
Incarvito, C
Rheingold, AL
Hartwig, JF
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (13) : 3224 - 3225
[3] Palladium-catalyzed intramolecular C-O bond formation
Kuwabe, S
Torraca, KE
Buchwald, SL
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (49) : 12202 - 12206
[4] Synthesis of Aryl Silacarboxylates via Palladium-Catalyzed C-O Bond Formation of Silacarboxylic Acids and Aryl Iodides
Liang, Jin-Yan
Shen, Shou-Jie
Xu, Xiao-Hu
Fu, Yun-Long
ORGANIC LETTERS, 2018, 20 (21) : 6627 - 6631
[5] Electronic dependence of C-O reductive elimination from palladium (aryl)neopentoxide complexes
Widenhoefer, RA
Buchwald, SL
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (26) : 6504 - 6511
[6] A Single Phosphine Ligand Allows Palladium-Catalyzed Intermolecular C-O Bond Formation with Secondary and Primary Alcohols
Wu, Xiaoxing
Fors, Brett P.
Buchwald, Stephen L.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (42) : 9943 - 9947
[7] Carbon-carbon bond formation via palladium-catalyzed reductive coupling of aryl halides in air and water
Venkatraman, S
Huang, T
Li, CJ
ADVANCED SYNTHESIS & CATALYSIS, 2002, 344 (3-4) : 399 - 405
[8] Palladium-Catalyzed Desulfitative Arylation by C-O Bond Cleavage of Aryl Inflates with Sodium Arylsulfinates
Zhou, Chao
Liu, Qingjiang
Li, Yaming
Zhang, Rong
Fu, Xinmei
Duan, Chunying
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (22): : 10468 - 10472
[9] A General and Efficient Catalyst for Palladium-Catalyzed C-O Coupling Reactions of Aryl Halides with Primary Alcohols
Gowrisankar, Saravanan
Sergeev, Alexey G.
Anbarasan, Pazhamalai
Spannenberg, Anke
Neumann, Helfried
Beller, Matthias
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (33) : 11592 - 11598
[10] Palladium-catalyzed intramolecular C-O bond formation: An approach to the synthesis of chiral benzodioxocines
Neogi, Arpita
Majhi, Tirtha P.
Achari, Basudeb
Chattopadhyay, Partha
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (02) : 330 - 336

← 1 2 3 4 →