Ni/Photoredox-Catalyzed C(sp2)-C(sp3) Cross-Coupling of Alkyl Pinacolboronates and (Hetero)Aryl Bromides

被引：3

作者：

Cauley, Anthony N. ^{[1
,2
]}

Ramirez, Antonio ^{[1
]}

Barhate, Chandan L. ^{[2
]}

Donnell, Andrew F. ^{[2
]}

Khandelwal, Purnima ^{[2
]}

Sezen-Edmonds, Melda ^{[1
]}

Sherwood, Trevor C. ^{[2
]}

Sloane, Jack L. ^{[2
]}

Cavallaro, Cullen L. ^{[2
]}

Simmons, Eric M. ^{[1
]}

机构：

[1] Bristol Myers Squibb Co, Chem Proc Dev, New Brunswick, NJ 08903 USA

[2] Bristol Myers Squibb Co, Small Mol Drug Discovery, Princeton, NJ 08543 USA

来源：

ORGANIC LETTERS | 2022年 / 24卷 / 31期

关键词：

SINGLE-ELECTRON TRANSMETALATION; LIGHT PHOTOREDOX CATALYSIS; SECONDARY; ACTIVATION; ARYLATION; ESTERS;

D O I：

10.1021/acs.orglett.2c01942

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Utilizing quinoline as a mild, catalytic additive, broadly applicable conditions for the Ni/photoredox-catalyzed C(sp(2))-C(sp(3)) cross-coupling of (hetero)aryl bromides and alkyl pinacolboronate esters were developed, which can be applied to both batch and flow reactions. In addition to primary benzylic nudeophiles, both stabilized and nonstabilized secondary alkyl boronic esters are effective coupling partners. Density functional theory calculations suggest that alkyl radical generation occurs from an alkyl-B(pin)-quinoline complex, which may proceed via an energy transfer process.

引用

页码：5663 / 5668

页数：6

共 50 条

[31] A Zinc Catalyzed C(sp3)-C(sp2) Suzuki-Miyaura Cross-Coupling Reaction Mediated by Aryl-Zincates
Procter, Richard J.
Dunsford, Jay J.
Rushworth, Philip J.
Hulcoop, David G.
Layfield, Richard A.
Ingleson, Michael J.
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (63) : 15889 - 15893
[32] Boryl radicals facilitate C(sp2)-C(sp3) cross-coupling reactions
Rodrigalvarez, Jesus
Martin, Ruben
[J]. NATURE SYNTHESIS, 2024,
[33] Highly Diastereoselective Cobalt-Mediated C(sp3)-C(sp2) Cross-Coupling Reactions of Cyclic Halohydrins with (Hetero) Aryl Grignard Reagents
Hammann, Jeffrey M.
Haas, Diana
Steib, Andreas K.
Knochel, Paul
[J]. SYNTHESIS-STUTTGART, 2015, 47 (10): : 1461 - 1468
[34] Photoredox Catalyzed C(sp3)-C(sp3) Coupling of α-Bromoesters and Triethylamine
Guerra, Allie W.
Pierce, Joshua G.
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2023, 89 (01): : 810 - 814
[35] A Rationally Designed Iron(II) Catalyst for C(sp3)-C(sp2) and C(sp3)-C(sp3) Suzuki-Miyaura Cross-Coupling
Chen, Donghuang
Lepori, Clement
Guillot, Regis
Gil, Richard
Bezzenine, Sophie
Hannedouche, Jerome
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2024, 63 (32)
[36] Enabling Deoxygenative C(sp2)-C(sp3) Cross-Coupling for Parallel Medicinal Chemistry
Liu, Wei
Mulhearn, James
Hao, Bo
Canellas, Santiago
Last, Stefaan
Gomez, Jose Enrique
Jones, Alexander
De Vera, Alexander
Kumar, Kiran
Rodriguez, Raquel
Van Eynde, Lars
Strambeanu, Iulia I.
Wolkenberg, Scott E.
[J]. ACS MEDICINAL CHEMISTRY LETTERS, 2023, 14 (06): : 853 - 859
[37] Photochemical C-H bond coupling for (hetero)aryl C(sp2)-C(sp3) bond construction
Zhao, Yating
Xia, Wujiong
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (20) : 4951 - 4963
[38] Palladium-Catalyzed Intramolecular Cross-Coupling of Unactivated C(sp3)-H and C(sp2)-H Bonds
Wu, Zhuo
Wu, Zechen
Sun, Xueliang
Qi, Weixin
Zhang, Zhengyang
Zhang, Yanghui
[J]. ORGANIC LETTERS, 2021, 23 (18) : 7161 - 7165
[39] Copper-Catalyzed Enantioconvergent Radical Suzuki-Miyaura C(sp3)-C(sp2) Cross-Coupling
Jiang, Sheng-Peng
Dong, Xiao-Yang
Gu, Qiang-Shuai
Ye, Liu
Li, Zhong-Liang
Liu, Xin-Yuan
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (46) : 19652 - 19659
[40] Pd-Catalyzed C(sp3)-C(sp2) cross-coupling of Y(CH2SiMe3)3(THF)2 with vinyl bromides and triflates
Cai, Guilong
Zhou, Zhibing
Wu, Wenchao
Yao, Bo
Zhang, Shaowen
Li, Xiaofang
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (37) : 8702 - 8706

← 1 2 3 4 5 →