Synthesis 2019; 51(10): 2171-2182
DOI: 10.1055/s-0037-1612216
paper
© Georg Thieme Verlag Stuttgart · New York

Copper-Catalyzed N-Arylation of Sulfoximines with Arylboronic Acids under Mild Conditions

Surabhi Gupta
a  Department of Chemistry, Indian Institute of Technology (BHU), 221005 Varanasi, Uttar Pradesh, India   Email: [email protected]
,
Siddharth Baranwal
a  Department of Chemistry, Indian Institute of Technology (BHU), 221005 Varanasi, Uttar Pradesh, India   Email: [email protected]
,
Nalluchamy Muniyappan
b  Department of Chemistry, Pondicherry University, 605014 Pondicherry, India
,
Shahulhameed Sabiah
b  Department of Chemistry, Pondicherry University, 605014 Pondicherry, India
,
a  Department of Chemistry, Indian Institute of Technology (BHU), 221005 Varanasi, Uttar Pradesh, India   Email: [email protected]
› Author Affiliations
J.K. gratefully acknowledges DST-India (DST/INT/MPG/P-09/2016) and Max-Planck Society, Germany for financial support through Indo-Max Planck partner group project. S.G. and S.B. acknowledge IIT (BHU) for a research fellowship.
Further Information

Publication History

Received: 07 December 2018

Accepted after revision: 16 January 2019

Publication Date:
19 February 2019 (online)


Abstract

N-Arylation of sulfoximines with different arylboronic acids, including sterically hindered boronic acids, is achieved using copper(I) iodide and 4-DMAP at room temperature. Moreover, N-arylation of biologically relevant l-methionine sulfoximine is demonstrated for the first time. All these reactions provided the desired products in excellent yields within a short span of time. The optimized reaction conditions are well suited to the task of N-vinylation of sulfoximine with trans-2-phenylvinylboronic acid.

Supporting Information

 
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