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Simplifying nickel(0) catalysis: an air-stable nickel precatalyst for the internally selective benzylation of terminal alkenes.
J Am Chem Soc 2013; 135(4):1585-92JA

Abstract

The synthesis and characterization of the air-stable nickel(II) complex trans-(PCy(2)Ph)(2)Ni(o-tolyl)Cl is described in conjunction with an investigation of its use for the Mizoroki-Heck-type, room temperature, internally selective coupling of substituted benzyl chlorides with terminal alkenes. This reaction, which employs a terminal alkene as an alkenylmetal equivalent, provides rapid, convergent access to substituted allylbenzene derivatives in high yield and with regioselectivity greater than 95:5 in nearly all cases. The reaction is operationally simple, can be carried out on the benchtop with no purification or degassing of solvents or reagents, and requires no exclusion of air or water during setup. Synthesis of the precatalyst is accomplished through a straightforward procedure that employs inexpensive, commercially available reagents, requires no purification steps, and proceeds in high yield.

Authors+Show Affiliations

Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.No affiliation info available

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural
Research Support, U.S. Gov't, Non-P.H.S.

Language

eng

PubMed ID

23316879

Citation

Standley, Eric A., and Timothy F. Jamison. "Simplifying Nickel(0) Catalysis: an Air-stable Nickel Precatalyst for the Internally Selective Benzylation of Terminal Alkenes." Journal of the American Chemical Society, vol. 135, no. 4, 2013, pp. 1585-92.
Standley EA, Jamison TF. 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.
Standley, E. A., & Jamison, T. F. (2013). Simplifying nickel(0) catalysis: an air-stable nickel precatalyst for the internally selective benzylation of terminal alkenes. Journal of the American Chemical Society, 135(4), pp. 1585-92. doi:10.1021/ja3116718.
Standley EA, Jamison TF. Simplifying Nickel(0) Catalysis: an Air-stable Nickel Precatalyst for the Internally Selective Benzylation of Terminal Alkenes. J Am Chem Soc. 2013 Jan 30;135(4):1585-92. PubMed PMID: 23316879.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Simplifying nickel(0) catalysis: an air-stable nickel precatalyst for the internally selective benzylation of terminal alkenes. AU - Standley,Eric A, AU - Jamison,Timothy F, Y1 - 2013/01/14/ PY - 2013/1/16/entrez PY - 2013/1/16/pubmed PY - 2013/7/24/medline SP - 1585 EP - 92 JF - Journal of the American Chemical Society JO - J. Am. Chem. Soc. VL - 135 IS - 4 N2 - The synthesis and characterization of the air-stable nickel(II) complex trans-(PCy(2)Ph)(2)Ni(o-tolyl)Cl is described in conjunction with an investigation of its use for the Mizoroki-Heck-type, room temperature, internally selective coupling of substituted benzyl chlorides with terminal alkenes. This reaction, which employs a terminal alkene as an alkenylmetal equivalent, provides rapid, convergent access to substituted allylbenzene derivatives in high yield and with regioselectivity greater than 95:5 in nearly all cases. The reaction is operationally simple, can be carried out on the benchtop with no purification or degassing of solvents or reagents, and requires no exclusion of air or water during setup. Synthesis of the precatalyst is accomplished through a straightforward procedure that employs inexpensive, commercially available reagents, requires no purification steps, and proceeds in high yield. SN - 1520-5126 UR - https://www.unboundmedicine.com/medline/citation/23316879/Simplifying_nickel_0__catalysis:_an_air_stable_nickel_precatalyst_for_the_internally_selective_benzylation_of_terminal_alkenes_ L2 - https://dx.doi.org/10.1021/ja3116718 DB - PRIME DP - Unbound Medicine ER -