Suzuki coupling of aroyl-MIDA boronate esters - A preliminary report on scope and limitations

被引：5

作者：

Lai, Samson ^{[1
]}

Takaesu, Noah ^{[1
]}

Lin, Wen Xuan ^{[1
]}

Perrin, David M. ^{[1
]}

机构：

[1] Univ British Columbia, Chem Dept, 2036 Main Mall, Vancouver, BC V6T 1Z1, Canada

来源：

TETRAHEDRON LETTERS | 2021年 / 74卷

基金：

加拿大自然科学与工程研究理事会;

关键词：

Acylboronate ester; Cross-coupling; Ketone; Acyl donor; POTASSIUM ACYLTRIFLUOROBORATES KATS; N-C CLEAVAGE; ARYLBORONIC ACIDS; CARBOXYLIC ANHYDRIDES; CATALYZED SYNTHESIS; KETONE SYNTHESIS; ACYL CHLORIDES; ARYL KETONES; REAGENTS; AMIDES;

D O I：

10.1016/j.tetlet.2021.153147

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Recent methodological reports for synthesizing acyl-MIDA boronate esters compel an investigation of their potential use as substrates in a standard Suzuki-Miyaura cross-coupling reaction. Here we report the production of benzophenones by C-C cross coupling between a benzoyl-MIDA boronate ester and a multitude of aryl bromide substrates in adequate yields following optimization under ambient conditions outside of a glove box. Under these standard conditions, none of several acyl-MIDA boronate esters (in an alkyl series) serves as a competent coupling partner. The substrate scope is also limited by the finding that the corresponding trifluoroborates of both acyl- and aroyltrifluroborates are not suitable substrates. For reasons of availability and synthetic difficulty in procuring other aroyl-MIDA boronates, this preliminary study examines the reactivity of benzoyl-MIDA boronate with several aryl bromide substrates. (C) 2021 Elsevier Ltd. All rights reserved.

引用

页数：5

共 12 条

[11] Copper-Catalysed Suzuki-Miyaura Cross-Coupling of Highly Fluorinated Aryl Boronate Esters with Aryl Iodides and Bromides and Fluoroarene-Arene π-Stacking Interactions in the Products
Budiman, Yudha P.
Friedrich, Alexandra
Radius, Udo
Marder, Todd B.
CHEMCATCHEM, 2019, 11 (21) : 5387 - 5396
[12] The scope and limitations of the Suzuki-Miyaura cross-coupling reactions of 6-and 8-substituted 1,2,3,4-tetrahydroisoquinoline-3-carboxylates
McKenna, JM
Moliterni, J
Qiao, Y
TETRAHEDRON LETTERS, 2001, 42 (34) : 5797 - 5800

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