A Photoredox Coupling Reaction of Benzylboronic Esters and Carbonyl Compounds in Batch and Flow

被引：23

作者：

Chen, Yiding ^{[1
]}

May, Oliver ^{[1
]}

Blakemore, David C. ^{[2
]}

Ley, Steven, V ^{[1
]}

机构：

[1] Univ Cambridge, Dept Chem, Lensfield Rd, Cambridge CB2 1EW, England

[2] Pfizer Inc, Med Design, Eastern Point Rd, Groton, CT 06340 USA

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 15期

基金：

欧盟地平线“2020”;

关键词：

ALDEHYDES; ACIDS; BENZYLATION; KETONES;

D O I：

10.1021/acs.orglett.9b02307

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Mild cross-coupling reaction between benzylboronic esters with carbonyl compounds and some imines was achieved under visible-light-induced iridium-catalyzed photoredox conditions. Functional group tolerance was demonstrated by 51 examples, including 13 heterocyclic compounds. Gram-scale reaction was realized through the use of computer-controlled continuous flow photoreactors.

引用

页码：6140 / 6144

页数：5

共 45 条

[1] Photoredox-Catalyzed Site-Selective α-C(sp3)-H Alkylation of Primary Amine Derivatives [J].

Ashley, Melissa A. ;

Yamauchi, Chiaki ;

Chu, John C. K. ;

Otsuka, Shinya ;

Yorimitsu, Hideki ;

Rovis, Tomislav .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (12) :4002-4006

[2] Acyl Radical Chemistry via Visible-Light Photoredox Catalysis [J].

Banerjee, Arghya ;

Lei, Zhen ;

Ngai, Ming-Yu .

SYNTHESIS-STUTTGART, 2019, 51 (02) :303-333

[3] Photocatalytic Barbier reaction - visible-light induced allylation and benzylation of aldehydes and ketones [J].

Berger, Anna Lucia ;

Donabauer, Karsten ;

Koenig, Burkhard .

CHEMICAL SCIENCE, 2018, 9 (36) :7230-7235

[4] Applications of Continuous-Flow Photochemistry in Organic Synthesis, Material Science, and Water Treatment [J].

Cambie, Dario ;

Bottecchia, Cecilia ;

Straathof, Natan J. W. ;

Hessel, Volker ;

Noel, Timothy .

CHEMICAL REVIEWS, 2016, 116 (17) :10276-10341

[5] The importance of synthetic chemistry in the pharmaceutical industry [J].

Campos, Kevin R. ;

Coleman, Paul J. ;

Alvarez, Juan C. ;

Dreher, Spencer D. ;

Garbaccio, Robert M. ;

Terrett, Nicholas K. ;

Tillyer, Richard D. ;

Truppo, Matthew D. ;

Parmee, Emma R. .

SCIENCE, 2019, 363 (6424) :244-+

[6] Acyl Radicals from Acylsilanes: Photoredox-Catalyzed Synthesis of Unsymmetrical Ketones [J].

Capaldo, Luca ;

Riccardi, Riccardo ;

RaveIli, Davide ;

Fagnoni, Maurizio .

ACS CATALYSIS, 2018, 8 (01) :304-309

[7] Site-Selective and Stereoselective C-H Alkylations of Carbohydrates via Combined Diarylborinic Acid and Photoredox Catalysis [J].

Dimakos, Victoria ;

Su, Hsin Y. ;

Garrett, Graham E. ;

Taylor, Mark S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (13) :5149-5153

[8] FREE RADICAL-MEDIATED RING EXPANSION AND RELATED ANNULATIONS [J].

DOWD, P ;

ZHANG, W .

CHEMICAL REVIEWS, 1993, 93 (06) :2091-2115

[9] Photoredox-Catalyzed Ketyl-Olefin Coupling for the Synthesis of Substituted Chromanols [J].

Fava, Eleonora ;

Nakajima, Masaki ;

Nguyen, Anh L. P. ;

Rueping, Magnus .

JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (16) :6959-6964

[10] POTENTIATION OF ACETOHEXAMIDE HYPOGLYCEMIA BY PHENYLBUTAZONE [J].

FIELD, JB ;

OHTA, M ;

BOYLE, C ;

REMER, A .

NEW ENGLAND JOURNAL OF MEDICINE, 1967, 277 (17) :889-&

← 1 2 3 4 5 →