One-Pot Reductive Amination and Suzuki-Miyaura Cross-Coupling of Formyl Aryl and Heteroaryl MIDA Boronates in Array Format

被引：31

作者：

Grob, Jonathan E. ^{[1
]}

Nunez, Jill ^{[1
]}

Dechantsreiter, Michael A. ^{[1
]}

Hamann, Lawrence G. ^{[1
]}

机构：

[1] Novartis Inst BioMed Res Inc, Cambridge, MA 02139 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 12期

关键词：

BORONIC ACIDS; BIOLOGICAL EVALUATION; EFFICIENT; COMPLEXES; RECEPTOR;

D O I：

10.1021/jo2005928

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Formyl-substituted aryl and heteroaryl MIDA boronates were prepared by a DMSO-free method and used in the first reported one-pot reductive amination-Suzuki-Miyaura cross-coupling sequence. This sequence was then carried out in parallel array format, using microwave-assisted in situ release cross-coupling of MLDA boronates to generate a library with diversity along two axes, affording rapid and convenient access to an array of druglike molecules.

引用

页码：4930 / 4940

页数：11

共 50 条

[1] Suzuki-Miyaura cross-coupling of alkenyl tosylates with alkenyl MIDA boronates
Luethy, Monique
Taylor, Richard J. K.
TETRAHEDRON LETTERS, 2012, 53 (27) : 3444 - 3447
[2] Facile and economical Miyaura borylation and one-pot Suzuki-Miyaura cross-coupling reaction
Boontiem, Phongsakorn
Kiatisevi, Supavadee
INORGANICA CHIMICA ACTA, 2020, 506
[3] Suzuki-Miyaura Cross-Coupling of Potassium Dioxolanylethyltrifluoroborate and Aryl/Heteroaryl Chlorides
Fleury-Bregeot, Nicolas
Oehlrich, Daniel
Rombouts, Frederik
Molander, Gary A.
ORGANIC LETTERS, 2013, 15 (07) : 1536 - 1539
[4] Suzuki-Miyaura cross-coupling reaction of aryl and heteroaryl pinacol boronates for the synthesis of 2-substituted pyrimidines
Asano, Shigehiro
Kamioka, Seiji
Isobe, Yoshiaki
TETRAHEDRON, 2012, 68 (01) : 272 - 279
[5] Development of the Direct Suzuki-Miyaura Cross-Coupling of Primary B-Alkyl MIDA-boronates and Aryl Bromides
St Denis, Jeffrey D.
Scully, Conor C. G.
Lee, C. Frank
Yudin, Andrei K.
ORGANIC LETTERS, 2014, 16 (05) : 1338 - 1341
[6] Dichloroimidazolidinedione-activated one-pot Suzuki-Miyaura cross-coupling of phenols
Madankar, Kamelia
Mokhtari, Javad
Mirjafary, Zohreh
APPLIED ORGANOMETALLIC CHEMISTRY, 2020, 34 (03)
[7] Suzuki-Miyaura cross-coupling reactions of potassium vinyltrifluoroborate with aryl and heteroaryl electrophiles
Molander, Gary A.
Brown, Adam R.
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (26): : 9681 - 9686
[8] A convenient one-pot access to phenanthridinones via Suzuki-Miyaura cross-coupling reaction
Tanimoto, Kouichi
Nakagawa, Naomichi
Takeda, Kazutaka
Kirihata, Mitsunori
Tanimori, Shinji
TETRAHEDRON LETTERS, 2013, 54 (28) : 3712 - 3714
[9] One-pot synthesis of chromenes by Suzuki-Miyaura cross-coupling reactions with benzyl bromides
Ahmed, Atiur
JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 2019, 96 (11) : 1429 - 1432
[10] Aryl and heteroaryl nosylates as stable and cheap partners for Suzuki-Miyaura cross-coupling reactions
Dikova, Anna
Cheval, Nicolas P.
Blanc, Aurelien
Weibel, Jean-Marc
Pale, Patrick
TETRAHEDRON, 2016, 72 (16) : 1960 - 1968

← 1 2 3 4 5 →