Pd-PEPPSI-IPent-SiO2: A Supported Catalyst for Challenging Negishi Coupling Reactions in Flow

Gregory A. Price; Abbas Hassan; Nalin Chandrasoma; Andrew R. Bogdan; Stevan W. Djuric; Michael G. Organ

doi:10.1002/anie.201708598

Pd-PEPPSI-IPent-SiO₂: A Supported Catalyst for Challenging Negishi Coupling Reactions in Flow

Gregory A. Price, Abbas Hassan, Nalin Chandrasoma, Andrew R. Bogdan, Stevan W. Djuric, Michael G. Organ

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

63 Citations (Scopus)

Abstract

A silica-supported precatalyst, Pd-PEPPSI-IPent-SiO₂, has been prepared and evaluated for its proficiency in the Negishi cross-coupling of hindered and electronically deactivated coupling partners. The precatalyst Pd-PEPPSI-IPent loaded onto packed bed columns shows high catalytic activity for the room-temperature coupling of deactivated/hindered biaryl partners. Also for the first time, the flowed Csp³–Csp² coupling of secondary alkylzinc reagents to (hetero)aromatics has been achieved with high selectivity with Pd-PEPPSI-IPent-SiO₂. These couplings required residence times as short as 3 minutes to effect completion of these challenging transformations with excellent selectivity for the nonrearranged product.

Original language	English
Pages (from-to)	13347-13350
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	56
Issue number	43
DOIs	https://doi.org/10.1002/anie.201708598
Publication status	Published - Oct 16 2017
Externally published	Yes

Keywords

arenes
cross-coupling
flow chemistry
N-heterocyclic carbenes
palladium

ASJC Scopus subject areas

Catalysis
General Chemistry

Access to Document

10.1002/anie.201708598

Cite this

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title = "Pd-PEPPSI-IPent-SiO2: A Supported Catalyst for Challenging Negishi Coupling Reactions in Flow",

abstract = "A silica-supported precatalyst, Pd-PEPPSI-IPent-SiO2, has been prepared and evaluated for its proficiency in the Negishi cross-coupling of hindered and electronically deactivated coupling partners. The precatalyst Pd-PEPPSI-IPent loaded onto packed bed columns shows high catalytic activity for the room-temperature coupling of deactivated/hindered biaryl partners. Also for the first time, the flowed Csp3–Csp2 coupling of secondary alkylzinc reagents to (hetero)aromatics has been achieved with high selectivity with Pd-PEPPSI-IPent-SiO2. These couplings required residence times as short as 3 minutes to effect completion of these challenging transformations with excellent selectivity for the nonrearranged product.",

keywords = "arenes, cross-coupling, flow chemistry, N-heterocyclic carbenes, palladium",

author = "Price, {Gregory A.} and Abbas Hassan and Nalin Chandrasoma and Bogdan, {Andrew R.} and Djuric, {Stevan W.} and Organ, {Michael G.}",

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T2 - A Supported Catalyst for Challenging Negishi Coupling Reactions in Flow

AU - Price, Gregory A.

AU - Hassan, Abbas

AU - Chandrasoma, Nalin

AU - Bogdan, Andrew R.

AU - Djuric, Stevan W.

AU - Organ, Michael G.

PY - 2017/10/16

Y1 - 2017/10/16

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KW - arenes

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KW - flow chemistry

KW - N-heterocyclic carbenes

KW - palladium

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