Chemo-, Regio-, and Enantioselective Rhodium-Catalyzed Allylation of Pyridazinones with Terminal Allenes

Shaista Parveen; Changkun Li; Abbas Hassan; Bernhard Breit

doi:10.1021/acs.orglett.7b00718

Chemo-, Regio-, and Enantioselective Rhodium-Catalyzed Allylation of Pyridazinones with Terminal Allenes

Shaista Parveen, Changkun Li, Abbas Hassan, Bernhard Breit

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

30 Citations (Scopus)

Abstract

The rhodium-catalyzed addition of pyridazinones to terminal allenes furnished the corresponding branched N²-allylated products in good yields with high regio- and enantioselectivities. A broad functional group compatibility was observed, and assorted synthetic transformations of the N-allylpyridazinones led to the preparation of a small library of N²-functionalized pyridazinones. Labeling experiments with deuterated substrates provided insights into the underlying reaction mechanism.

Original language	English
Pages (from-to)	2326-2329
Number of pages	4
Journal	Organic Letters
Volume	19
Issue number	9
DOIs	https://doi.org/10.1021/acs.orglett.7b00718
Publication status	Published - May 5 2017
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/acs.orglett.7b00718

Cite this

@article{7117cccc47c24ebba2d6252044e8d245,

title = "Chemo-, Regio-, and Enantioselective Rhodium-Catalyzed Allylation of Pyridazinones with Terminal Allenes",

abstract = "The rhodium-catalyzed addition of pyridazinones to terminal allenes furnished the corresponding branched N2-allylated products in good yields with high regio- and enantioselectivities. A broad functional group compatibility was observed, and assorted synthetic transformations of the N-allylpyridazinones led to the preparation of a small library of N2-functionalized pyridazinones. Labeling experiments with deuterated substrates provided insights into the underlying reaction mechanism.",

author = "Shaista Parveen and Changkun Li and Abbas Hassan and Bernhard Breit",

note = "Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",

year = "2017",

month = may,

day = "5",

doi = "10.1021/acs.orglett.7b00718",

language = "English",

volume = "19",

pages = "2326--2329",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "9",

}

TY - JOUR

T1 - Chemo-, Regio-, and Enantioselective Rhodium-Catalyzed Allylation of Pyridazinones with Terminal Allenes

AU - Parveen, Shaista

AU - Li, Changkun

AU - Hassan, Abbas

AU - Breit, Bernhard

PY - 2017/5/5

Y1 - 2017/5/5

N2 - The rhodium-catalyzed addition of pyridazinones to terminal allenes furnished the corresponding branched N2-allylated products in good yields with high regio- and enantioselectivities. A broad functional group compatibility was observed, and assorted synthetic transformations of the N-allylpyridazinones led to the preparation of a small library of N2-functionalized pyridazinones. Labeling experiments with deuterated substrates provided insights into the underlying reaction mechanism.

AB - The rhodium-catalyzed addition of pyridazinones to terminal allenes furnished the corresponding branched N2-allylated products in good yields with high regio- and enantioselectivities. A broad functional group compatibility was observed, and assorted synthetic transformations of the N-allylpyridazinones led to the preparation of a small library of N2-functionalized pyridazinones. Labeling experiments with deuterated substrates provided insights into the underlying reaction mechanism.

UR - http://www.scopus.com/inward/record.url?scp=85019034663&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85019034663&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.7b00718

DO - 10.1021/acs.orglett.7b00718

M3 - Article

C2 - 28422507

AN - SCOPUS:85019034663

SN - 1523-7060

VL - 19

SP - 2326

EP - 2329

JO - Organic Letters

JF - Organic Letters

IS - 9

ER -

Chemo-, Regio-, and Enantioselective Rhodium-Catalyzed Allylation of Pyridazinones with Terminal Allenes

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this