Trans -chloro(1-naphthyl)bis(triphenylphosphine)nickel(II)/PCy 3 catalyzed cross-coupling of aryl and heteroaryl neopentylglycolboronates with aryl and heteroaryl mesylates and sulfamates at room temperature

Pawaret Leowanawat; Na Zhang; Mehtap Safi; David J. Hoffman; Miriam C. Fryberger; Aiswaria George; Virgil Percec

doi:10.1021/jo3001194

Trans -chloro(1-naphthyl)bis(triphenylphosphine)nickel(II)/PCy ₃ catalyzed cross-coupling of aryl and heteroaryl neopentylglycolboronates with aryl and heteroaryl mesylates and sulfamates at room temperature

Pawaret Leowanawat
, Na Zhang
, Mehtap Safi
, David J. Hoffman
, Miriam C. Fryberger
, Aiswaria George
, Virgil Percec

University of Pennsylvania School of Arts and Sciences

Research output: Contribution to journal › Article › peer-review

75 Citations (Scopus)

Abstract

trans-Chloro(1-naphthyl)bis(triphenylphosphine)nickel(II) complex/PCy ₃ system has been successfully applied as catalyst for the Suzuki-Miyaura cross-coupling of aryl and heteroaryl neopentylglycolboronates with aryl and heteroaryl mesylates and sulfamates in THF at room temperature. This cross-coupling reaction tolerates various functional groups, including keto, imino, ester, ether, and cyano. Together with the nickel-catalyzed, one-pot, two-step neopentylglycolborylation, this bench stable and inexpensive Ni(II)-based catalyst can be utilized as an alternative to Ni(COD) ₂/PCy ₃ to provide an inexpensive, robust, and convenient synthesis of biaryl and heterobiaryl compounds.

Original language	English
Pages (from-to)	2885-2892
Number of pages	8
Journal	Journal of Organic Chemistry
Volume	77
Issue number	6
DOIs	https://doi.org/10.1021/jo3001194
Publication status	Published - 16 Mar 2012
Externally published	Yes

Access to Document

10.1021/jo3001194

Fingerprint

Dive into the research topics of 'Trans -chloro(1-naphthyl)bis(triphenylphosphine)nickel(II)/PCy ₃ catalyzed cross-coupling of aryl and heteroaryl neopentylglycolboronates with aryl and heteroaryl mesylates and sulfamates at room temperature'. Together they form a unique fingerprint.

Cite this

Leowanawat, P., Zhang, N., Safi, M., Hoffman, D. J., Fryberger, M. C., George, A., & Percec, V. (2012). Trans -chloro(1-naphthyl)bis(triphenylphosphine)nickel(II)/PCy ₃ catalyzed cross-coupling of aryl and heteroaryl neopentylglycolboronates with aryl and heteroaryl mesylates and sulfamates at room temperature. Journal of Organic Chemistry, 77(6), 2885-2892. https://doi.org/10.1021/jo3001194

@article{4f518f19def64f7597416813fbd819f5,

title = "Trans -chloro(1-naphthyl)bis(triphenylphosphine)nickel(II)/PCy 3 catalyzed cross-coupling of aryl and heteroaryl neopentylglycolboronates with aryl and heteroaryl mesylates and sulfamates at room temperature",

abstract = "trans-Chloro(1-naphthyl)bis(triphenylphosphine)nickel(II) complex/PCy 3 system has been successfully applied as catalyst for the Suzuki-Miyaura cross-coupling of aryl and heteroaryl neopentylglycolboronates with aryl and heteroaryl mesylates and sulfamates in THF at room temperature. This cross-coupling reaction tolerates various functional groups, including keto, imino, ester, ether, and cyano. Together with the nickel-catalyzed, one-pot, two-step neopentylglycolborylation, this bench stable and inexpensive Ni(II)-based catalyst can be utilized as an alternative to Ni(COD) 2/PCy 3 to provide an inexpensive, robust, and convenient synthesis of biaryl and heterobiaryl compounds.",

author = "Pawaret Leowanawat and Na Zhang and Mehtap Safi and Hoffman, \{David J.\} and Fryberger, \{Miriam C.\} and Aiswaria George and Virgil Percec",

year = "2012",

month = mar,

day = "16",

doi = "10.1021/jo3001194",

language = "English",

volume = "77",

pages = "2885--2892",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "6",

}

Leowanawat, P, Zhang, N, Safi, M, Hoffman, DJ, Fryberger, MC, George, A & Percec, V 2012, 'Trans -chloro(1-naphthyl)bis(triphenylphosphine)nickel(II)/PCy ₃ catalyzed cross-coupling of aryl and heteroaryl neopentylglycolboronates with aryl and heteroaryl mesylates and sulfamates at room temperature', Journal of Organic Chemistry, vol. 77, no. 6, pp. 2885-2892. https://doi.org/10.1021/jo3001194

Trans -chloro(1-naphthyl)bis(triphenylphosphine)nickel(II)/PCy ₃ catalyzed cross-coupling of aryl and heteroaryl neopentylglycolboronates with aryl and heteroaryl mesylates and sulfamates at room temperature. / Leowanawat, Pawaret; Zhang, Na; Safi, Mehtap et al.
In: Journal of Organic Chemistry, Vol. 77, No. 6, 16.03.2012, p. 2885-2892.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Trans -chloro(1-naphthyl)bis(triphenylphosphine)nickel(II)/PCy 3 catalyzed cross-coupling of aryl and heteroaryl neopentylglycolboronates with aryl and heteroaryl mesylates and sulfamates at room temperature

AU - Leowanawat, Pawaret

AU - Zhang, Na

AU - Safi, Mehtap

AU - Hoffman, David J.

AU - Fryberger, Miriam C.

AU - George, Aiswaria

AU - Percec, Virgil

PY - 2012/3/16

Y1 - 2012/3/16

N2 - trans-Chloro(1-naphthyl)bis(triphenylphosphine)nickel(II) complex/PCy 3 system has been successfully applied as catalyst for the Suzuki-Miyaura cross-coupling of aryl and heteroaryl neopentylglycolboronates with aryl and heteroaryl mesylates and sulfamates in THF at room temperature. This cross-coupling reaction tolerates various functional groups, including keto, imino, ester, ether, and cyano. Together with the nickel-catalyzed, one-pot, two-step neopentylglycolborylation, this bench stable and inexpensive Ni(II)-based catalyst can be utilized as an alternative to Ni(COD) 2/PCy 3 to provide an inexpensive, robust, and convenient synthesis of biaryl and heterobiaryl compounds.

AB - trans-Chloro(1-naphthyl)bis(triphenylphosphine)nickel(II) complex/PCy 3 system has been successfully applied as catalyst for the Suzuki-Miyaura cross-coupling of aryl and heteroaryl neopentylglycolboronates with aryl and heteroaryl mesylates and sulfamates in THF at room temperature. This cross-coupling reaction tolerates various functional groups, including keto, imino, ester, ether, and cyano. Together with the nickel-catalyzed, one-pot, two-step neopentylglycolborylation, this bench stable and inexpensive Ni(II)-based catalyst can be utilized as an alternative to Ni(COD) 2/PCy 3 to provide an inexpensive, robust, and convenient synthesis of biaryl and heterobiaryl compounds.

UR - https://www.scopus.com/pages/publications/84858680177

U2 - 10.1021/jo3001194

DO - 10.1021/jo3001194

M3 - Article

AN - SCOPUS:84858680177

SN - 0022-3263

VL - 77

SP - 2885

EP - 2892

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 6