C-H to C-N Cross-Coupling of Sulfonamides with Olefins

Rulin Ma; M. Christina White

doi:10.1021/jacs.7b13492

C-H to C-N Cross-Coupling of Sulfonamides with Olefins

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

Abstract

Cross-coupling of nitrogen with hydrocarbons under fragment coupling conditions stands to significantly impact chemical synthesis. Herein, we disclose a C(sp³)-N fragment coupling reaction between terminal olefins and N-triflyl protected aliphatic and aromatic amines via Pd(II)/SOX (sulfoxide-oxazoline) catalyzed intermolecular allylic C-H amination. A range of (56) allylic amines are furnished in good yields (avg. 75%) and excellent regio- and stereoselectivity (avg. >20:1 linear:branched, >20:1 E:Z). Mechanistic studies reveal that the SOX ligand framework is effective at promoting functionalization by supporting cationic π-allyl Pd.

Original language	English (US)
Pages (from-to)	3202-3205
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	140
Issue number	9
DOIs	https://doi.org/10.1021/jacs.7b13492
State	Published - Mar 7 2018

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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@article{f6d2697030004bf68d223acdbd5646ed,

title = "C-H to C-N Cross-Coupling of Sulfonamides with Olefins",

abstract = "Cross-coupling of nitrogen with hydrocarbons under fragment coupling conditions stands to significantly impact chemical synthesis. Herein, we disclose a C(sp3)-N fragment coupling reaction between terminal olefins and N-triflyl protected aliphatic and aromatic amines via Pd(II)/SOX (sulfoxide-oxazoline) catalyzed intermolecular allylic C-H amination. A range of (56) allylic amines are furnished in good yields (avg. 75%) and excellent regio- and stereoselectivity (avg. >20:1 linear:branched, >20:1 E:Z). Mechanistic studies reveal that the SOX ligand framework is effective at promoting functionalization by supporting cationic π-allyl Pd.",

author = "Rulin Ma and {Christina White}, M.",

note = "Funding Information: Financial support NIGMS MIRA (R35 GM122525). We thank W. Liu Dr. S. Ammann for preliminary ligand studies; Dr. J. Clark, Dr. J. Griffin for checking experimental procedure; Dr. L. Zhu for NMR data analysis, and Johnson Matthey for Pd(OAc).",

year = "2018",

month = mar,

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doi = "10.1021/jacs.7b13492",

language = "English (US)",

volume = "140",

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journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

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T1 - C-H to C-N Cross-Coupling of Sulfonamides with Olefins

AU - Ma, Rulin

AU - Christina White, M.

N1 - Funding Information: Financial support NIGMS MIRA (R35 GM122525). We thank W. Liu Dr. S. Ammann for preliminary ligand studies; Dr. J. Clark, Dr. J. Griffin for checking experimental procedure; Dr. L. Zhu for NMR data analysis, and Johnson Matthey for Pd(OAc).

PY - 2018/3/7

Y1 - 2018/3/7

N2 - Cross-coupling of nitrogen with hydrocarbons under fragment coupling conditions stands to significantly impact chemical synthesis. Herein, we disclose a C(sp3)-N fragment coupling reaction between terminal olefins and N-triflyl protected aliphatic and aromatic amines via Pd(II)/SOX (sulfoxide-oxazoline) catalyzed intermolecular allylic C-H amination. A range of (56) allylic amines are furnished in good yields (avg. 75%) and excellent regio- and stereoselectivity (avg. >20:1 linear:branched, >20:1 E:Z). Mechanistic studies reveal that the SOX ligand framework is effective at promoting functionalization by supporting cationic π-allyl Pd.

AB - Cross-coupling of nitrogen with hydrocarbons under fragment coupling conditions stands to significantly impact chemical synthesis. Herein, we disclose a C(sp3)-N fragment coupling reaction between terminal olefins and N-triflyl protected aliphatic and aromatic amines via Pd(II)/SOX (sulfoxide-oxazoline) catalyzed intermolecular allylic C-H amination. A range of (56) allylic amines are furnished in good yields (avg. 75%) and excellent regio- and stereoselectivity (avg. >20:1 linear:branched, >20:1 E:Z). Mechanistic studies reveal that the SOX ligand framework is effective at promoting functionalization by supporting cationic π-allyl Pd.

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