Synthesis of Pyrrolidines and Piperidines via Palladium-Catalyzed Coupling of Vinylic Halides and Olefinic Sulfonamides

Richard C. Larock; Hoseok Yang; Steven M. Weinreb; R. Jason Herr

doi:10.1021/jo00094a031

Synthesis of Pyrrolidines and Piperidines via Palladium-Catalyzed Coupling of Vinylic Halides and Olefinic Sulfonamides

Richard C. Larock
, Hoseok Yang
, Steven M. Weinreb
, R. Jason Herr

Chemistry

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

68 Scopus citations

Abstract

The palladium-catalyzed coupling of vinylic halides and olefinic sulfonamides affords good yields of 2-(1-alkenyl)pyrrolidine and -piperidine sulfonamides via vinylpalladium addition to the olefin, regioselective rearrangement to a π-allylpalladium intermediate, and subsequent intramolecular nucleophilic displacement of palladium.

Original language	English (US)
Pages (from-to)	4172-4178
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	59
Issue number	15
DOIs	https://doi.org/10.1021/jo00094a031
State	Published - Jul 1 1994

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1021/jo00094a031

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title = "Synthesis of Pyrrolidines and Piperidines via Palladium-Catalyzed Coupling of Vinylic Halides and Olefinic Sulfonamides",

abstract = "The palladium-catalyzed coupling of vinylic halides and olefinic sulfonamides affords good yields of 2-(1-alkenyl)pyrrolidine and -piperidine sulfonamides via vinylpalladium addition to the olefin, regioselective rearrangement to a π-allylpalladium intermediate, and subsequent intramolecular nucleophilic displacement of palladium.",

author = "Larock, \{Richard C.\} and Hoseok Yang and Weinreb, \{Steven M.\} and Herr, \{R. Jason\}",

year = "1994",

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doi = "10.1021/jo00094a031",

language = "English (US)",

volume = "59",

pages = "4172--4178",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "15",

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T1 - Synthesis of Pyrrolidines and Piperidines via Palladium-Catalyzed Coupling of Vinylic Halides and Olefinic Sulfonamides

AU - Larock, Richard C.

AU - Yang, Hoseok

AU - Weinreb, Steven M.

AU - Herr, R. Jason

PY - 1994/7/1

Y1 - 1994/7/1

N2 - The palladium-catalyzed coupling of vinylic halides and olefinic sulfonamides affords good yields of 2-(1-alkenyl)pyrrolidine and -piperidine sulfonamides via vinylpalladium addition to the olefin, regioselective rearrangement to a π-allylpalladium intermediate, and subsequent intramolecular nucleophilic displacement of palladium.

AB - The palladium-catalyzed coupling of vinylic halides and olefinic sulfonamides affords good yields of 2-(1-alkenyl)pyrrolidine and -piperidine sulfonamides via vinylpalladium addition to the olefin, regioselective rearrangement to a π-allylpalladium intermediate, and subsequent intramolecular nucleophilic displacement of palladium.

UR - https://www.scopus.com/pages/publications/0028147903

UR - https://www.scopus.com/pages/publications/0028147903#tab=citedBy

U2 - 10.1021/jo00094a031

DO - 10.1021/jo00094a031

M3 - Article

AN - SCOPUS:0028147903

SN - 0022-3263

VL - 59

SP - 4172

EP - 4178

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 15

ER -

Synthesis of Pyrrolidines and Piperidines via Palladium-Catalyzed Coupling of Vinylic Halides and Olefinic Sulfonamides

Abstract

All Science Journal Classification (ASJC) codes

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