Miyaura Borylation and One-Pot Two-Step Homocoupling of Aryl Chlorides and Bromides under Solvent-Free Conditions

被引：54

作者：

Dzhevakov, Pavel B. ^{[1
]}

Topchiy, Maxim A. ^{[1
]}

Zharkova, Daria A. ^{[2
]}

Morozov, Oleg S. ^{[1
]}

Asachenko, Andrey F. ^{[1
]}

Nechaev, Mikhail S. ^{[1
,2
]}

机构：

[1] Russian Acad Sci, AV Topchiev Petrochem Synth Inst, Moscow 119991, Russia

[2] Moscow MV Lomonosov State Univ, Moscow 119991, Russia

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2016年 / 358卷 / 06期

关键词：

cross-coupling reactions; homocoupling; Miyaura borylation; palladium; solvent-free reactions; CROSS-COUPLING REACTION; PALLADIUM-CATALYZED BORYLATION; ORGANIC-SYNTHESIS; HALIDES; MICROWAVE;

D O I：

10.1002/adsc.201500844

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Solvent-free protocols for Miyaura borylation and the one-pot, two-step homocoupling of aryl halides are reported for the first time. Bis(di-benzylideneacetone) palladium(0) [Pd(dba)(2)] is an optimal source of palladium for Miyaura borylation, while for one-pot two-step homocoupling palladium(II) acetate [Pd(OAc)(2)] gives highest yields. Aryl bromides are coupled most efficiently using the DPEphos ligand. Chlorides are coupled using XPhos. The developed protocols are robust, versatile and easily reproducible on a large scale.

引用

页码：977 / 983

页数：7

共 37 条

[11] Microwave-assisted synthesis of pinacol boronates from aryl chlorides catalyzed by a palladium/imidazolium salt system
Fürstner, A
Seidel, G
[J]. ORGANIC LETTERS, 2002, 4 (04) : 541 - 543
[12] Hall DG, 2005, BORONIC ACIDS: PREPARATION AND APPLICATIONS IN ORGANIC SYNTHESIS AND MEDICINE, P1, DOI 10.1002/3527606548.ch1
[13] Metal-catalyzed reactions of diborons for synthesis of organoboron compounds
Ishiyama, T
Miyaura, N
[J]. CHEMICAL RECORD, 2004, 3 (05) : 271 - 280
[14] Transition metal-catalyzed borylation of alkanes and arenes via C-H activation
Ishiyama, T
Miyaura, N
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2003, 680 (1-2) : 3 - 11
[15] Synthesis of pinacol arylboronates via cross-coupling reaction of bis(pinacolato)diboron with chloroarenes catalyzed by palladium(0)-tricyclohexylphosphine complexes
Ishiyama, T
Ishida, K
Miyaura, N
[J]. TETRAHEDRON, 2001, 57 (49) : 9813 - 9816
[16] Synthesis of arylboronates via the palladium(O)-catalyzed cross-coupling reaction of tetra(alkoxo)diborons with aryl triflates
Ishiyama, T
Itoh, Y
Kitano, T
Miyaura, N
[J]. TETRAHEDRON LETTERS, 1997, 38 (19) : 3447 - 3450
[17] PALLADIUM(O)-CATALYZED CROSS-COUPLING REACTION OF ALKOXYDIBORON WITH HALOARENES - A DIRECT PROCEDURE FOR ARYLBORONIC ESTERS
ISHIYAMA, T
MURATA, M
MIYAURA, N
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (23) : 7508 - 7510
[18] Kawamorita S., 2011, J AM CHEM SOC, V123, P8513
[19] Palladium-Catalyzed Borylation of Sterically Demanding Aryl Halides with a Silica-Supported Compact Phosphane Ligand
Kawamorita, Soichiro
Ohmiya, Hirohisa
Iwai, Tomohiro
Sawamura, Masaya
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (36) : 8363 - 8366
[20] Expanded ring diaminocarbene palladium complexes: synthesis, structure, and Suzuki-Miyaura cross-coupling of heteroaryl chlorides in water
Kolychev, Eugene L.
Asachenko, Andrey F.
Dzhevakov, Pavel B.
Bush, Alexander A.
Shuntikov, Viacheslav V.
Khrustalev, Victor N.
Nechaev, Mikhail S.
[J]. DALTON TRANSACTIONS, 2013, 42 (19) : 6859 - 6866

← 1 2 3 4 →