In-Situ Bromination Enables Formal Cross-Electrophile Coupling of Alcohols with Aryl and Alkenyl Halides

被引：64

作者：

Chi, Benjamin K. ^{[1
]}

Widness, Jonas K. ^{[1
]}

Gilbert, Michael M. ^{[1
]}

Salgueiro, Daniel C. ^{[1
]}

Garcia, Kevin J. ^{[1
]}

Weix, Daniel J. ^{[1
]}

机构：

[1] Univ Wisconsin, Dept Chem, Madison, WI 53706 USA

来源：

ACS CATALYSIS | 2022年 / 12卷 / 01期

关键词：

alcohol; bromination; nickel catalysis; cross-electrophile coupling; cross-coupling; phosphonium; high-throughput experimentation; C(sp(2))-C(sp(3)) bond formation; HENDRICKSON REAGENT; BENZYL ALCOHOLS; ALKYL BROMIDES; CATALYSIS; DIARYLMETHANES; OXALATES; NI;

D O I：

10.1021/acscatal.1c05208

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Although alcohols are one of the largest pools of alkyl substrates, approaches to utilize them in cross-coupling and cross-electrophile coupling are limited. We report the use of 1 degrees and 2 degrees alcohols in cross-electrophile coupling with aryl and vinyl halides to form C(sp(3))-C(sp(2)) bonds in a one-pot strategy utilizing a very fast (<1 min) bromination. The reaction's simple benchtop setup and broad scope (42 examples, 56% +/- 15% average yield) facilitates use at all scales. The potential in parallel synthesis applications was demonstrated by successfully coupling all combinations of 8 alcohols with 12 aryl cores in a 96-well plate.

引用

收藏

页码：580 / 586

页数：7

相关论文

共 51 条

[1]

Ackerman LKG, 2015, CHEM SCI, V6, P1115, DOI [10.1039/c4sc03106g, 10.1039/C4SC03106G]

[2] ChemBead Enabled High-Throughput Cross-Electrophile Coupling Reveals a New Complementary Ligand [J].

Aguirre, Ana L. ;

Loud, Nathan L. ;

Johnson, Keywan A. ;

Weix, Daniel J. ;

Wang, Ying .

CHEMISTRY-A EUROPEAN JOURNAL, 2021, 27 (51) :12981-12986

[3] Updating and further expanding GSK's solvent sustainability guide [J].

Alder, Catherine M. ;

Hayler, John D. ;

Henderson, Richard K. ;

Redman, Aniko M. ;

Shukla, Lena ;

Shuster, Leanna E. ;

Sneddon, Helen F. .

GREEN CHEMISTRY, 2016, 18 (13) :3879-3890

[4] Nickel-Catalyzed Cross-Electrophile Coupling with Organic Reductants in Non-Amide Solvents [J].

Anka-Lufford, Lukiana L. ;

Huihui, Kierra M. M. ;

Gower, Nicholas J. ;

Ackerman, Laura K. G. ;

Weix, Daniel J. .

CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (33) :11564-11567

[5] A Process Chemistry Benchmark for sp2-sp3 Cross Couplings [J].

Beutner, Gregory L. ;

Simmons, Eric M. ;

Ayers, Sloan ;

Bemis, Christopher Y. ;

Goldfogel, Matthew J. ;

Joe, Candice L. ;

Marshall, Jonathan ;

Wisniewski, Steven R. .

JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (15) :10380-10396

[6] Mechanism and Selectivity in Nickel-Catalyzed Cross-Electrophile Coupling of Aryl Halides with Alkyl Halides [J].

Biswas, Soumik ;

Weix, Daniel J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (43) :16192-16197

[7] Organic Electron Donors as Powerful Single-Electron Reducing Agents in Organic Synthesis [J].

Broggi, Julie ;

Terme, Thierry ;

Vanelle, Patrice .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (02) :384-413

[8] Direct cross-coupling of benzyl alcohols to construct diarylmethanes via palladium catalysis [J].

Cao, Zhi-Chao ;

Yu, Da-Gang ;

Zhu, Ru-Yi ;

Wei, Jiang-Bo ;

Shi, Zhang-Jie .

CHEMICAL COMMUNICATIONS, 2015, 51 (13) :2683-2686

[9] Analysis of the reactions used for the preparation of drug candidate molecules [J].

Carey, John S. ;

Laffan, David ;

Thomson, Colin ;

Williams, Mike T. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (12) :2337-2347

[10] A Widely Applicable Dual Catalytic System for Cross-Electrophile Coupling Enabled by Mechanistic Studies [J].

Charboneau, David J. ;

Barth, Emily L. ;

Hazari, Nilay ;

Uehling, Mycah R. ;

Zultanski, Susan L. .

ACS CATALYSIS, 2020, 10 (21) :12642-12656

← 1 2 3 4 5 6 →