Bench-Stable Nickel Precatalysts with Heck-type Activation

Overview

Journal Organometallics

Publisher American Chemical Society

Date 2018 Sep 4

PMID 30174368

Citations 4

Authors

Jessica M Weber

Ashley R Longstreet

Timothy F Jamison

Affiliations

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Abstract

Herein, we report the synthesis and characterization of a new class of air- and moisture-stable phosphine-containing nickel(II) precatalysts, which activate through a Heck-type mechanism. The activities of the precatalysts are demonstrated with a carbonyl-ene coupling reaction.

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References

Tasker S, Standley E, Jamison T . Recent advances in homogeneous nickel catalysis. Nature. 2014; 509(7500):299-309. PMC: 4344729. DOI: 10.1038/nature13274. View

Standley E, Smith S, Muller P, Jamison T . A Broadly Applicable Strategy for Entry into Homogeneous Nickel(0) Catalysts from Air-Stable Nickel(II) Complexes. Organometallics. 2014; 33(8):2012-2018. PMC: 4006606. DOI: 10.1021/om500156q. View

Rosen B, Quasdorf K, Wilson D, Zhang N, Resmerita A, Garg N . Nickel-catalyzed cross-couplings involving carbon-oxygen bonds. Chem Rev. 2010; 111(3):1346-416. PMC: 3055945. DOI: 10.1021/cr100259t. View

Chen C, Yang L . Ni(II)-(sigma-aryl) complex: a facile, efficient catalyst for nickel-catalyzed carbon-nitrogen coupling reactions. J Org Chem. 2007; 72(16):6324-7. DOI: 10.1021/jo0709448. View

Strieth-Kalthoff F, Longstreet A, Weber J, Jamison T . Bench-Stable -Heterocyclic Carbene Nickel Precatalysts for C-C and C-N Bond-Forming Reactions. ChemCatChem. 2018; 10(13):2873-2877. PMC: 6099443. DOI: 10.1002/cctc.201800454. View

Ge S, Hartwig J . Highly reactive, single-component nickel catalyst precursor for Suzuki-Miyuara cross-coupling of heteroaryl boronic acids with heteroaryl halides. Angew Chem Int Ed Engl. 2012; 51(51):12837-41. PMC: 3613336. DOI: 10.1002/anie.201207428. View

Shields J, Gray E, Doyle A . A modular, air-stable nickel precatalyst. Org Lett. 2015; 17(9):2166-9. PMC: 4719147. DOI: 10.1021/acs.orglett.5b00766. View

Ho C, Ng S, Jamison T . Nickel-catalyzed, carbonyl-ene-type reactions: selective for alpha olefins and more efficient with electron-rich aldehydes. J Am Chem Soc. 2006; 128(16):5362-3. PMC: 3148195. DOI: 10.1021/ja061471+. View

Jezorek R, Zhang N, Leowanawat P, Bunner M, Gutsche N, Pesti A . Air-stable nickel precatalysts for fast and quantitative cross-coupling of aryl sulfamates with aryl neopentylglycolboronates at room temperature. Org Lett. 2014; 16(24):6326-9. DOI: 10.1021/ol503061c. View

10.

Ng S, Ho C, Jamison T . Nickel-catalyzed coupling of alkenes, aldehydes, and silyl triflates. J Am Chem Soc. 2006; 128(35):11513-28. PMC: 3148200. DOI: 10.1021/ja062866w. View

11.

Standley E, Tasker S, Jensen K, Jamison T . Nickel Catalysis: Synergy between Method Development and Total Synthesis. Acc Chem Res. 2015; 48(5):1503-14. PMC: 4586268. DOI: 10.1021/acs.accounts.5b00064. View

12.

Dander J, Weires N, Garg N . Benchtop Delivery of Ni(cod)2 using Paraffin Capsules. Org Lett. 2016; 18(15):3934-6. PMC: 7010371. DOI: 10.1021/acs.orglett.6b01758. View

13.

Park N, Teverovskiy G, Buchwald S . Development of an air-stable nickel precatalyst for the amination of aryl chlorides, sulfamates, mesylates, and triflates. Org Lett. 2013; 16(1):220-3. PMC: 3926134. DOI: 10.1021/ol403209k. View

14.

Standley E, Jamison T . Simplifying nickel(0) catalysis: an air-stable nickel precatalyst for the internally selective benzylation of terminal alkenes. J Am Chem Soc. 2013; 135(4):1585-92. PMC: 3564234. DOI: 10.1021/ja3116718. View

15.

Ng S, Jamison T . Simple alkenes as substitutes for organometallic reagents: nickel-catalyzed, intermolecular coupling of aldehydes, silyl triflates, and alpha olefins. J Am Chem Soc. 2005; 127(41):14194-5. DOI: 10.1021/ja055363j. View