Synthesis 2018; 50(06): 1275-1283
DOI: 10.1055/s-0036-1591846
paper
© Georg Thieme Verlag Stuttgart · New York

Copper-Catalyzed Base-Controlled Diastereoselective Synthesis of Tetraarylethanes from 2-Benzylpyridines

Selvaraj Chandrasekar
Department of Chemistry, Indian Institute of Technology Madras, Chennai-600036, Tamil Nadu, India   Email: gsekar@iitm.ac.in
,
Iyyanar Karthikeyan
Department of Chemistry, Indian Institute of Technology Madras, Chennai-600036, Tamil Nadu, India   Email: gsekar@iitm.ac.in
,
Department of Chemistry, Indian Institute of Technology Madras, Chennai-600036, Tamil Nadu, India   Email: gsekar@iitm.ac.in
› Author Affiliations
We thank DST (project No: SB/S1/OC-72/2013) and DST nano mission [SR/NM/NS-1034/2012(G)] for financial support. SCS thanks UGC, New Delhi for a research fellowship.
Further Information

Publication History

Received: 25 May 2017

Accepted after revision: 07 November 2017

Publication Date:
11 December 2017 (online)


Dedicated to Prof. M. Periyasamy on the occasion of his 65th birthday.

Abstract

A highly efficient and base-controlled diastereoselective synthesis of tetraarylethanes through copper-catalyzed dehydrogenative homocoupling of readily available 2-benzylpyridines is reported. Various dl- and meso-tetraarylethanes were diastereoseletively synthesized by this new protocol, where base plays the role of the principle modulator: Grignard reagents selectively provide the C2 isomers, whereas KOt-Bu promotes the formation of the meso-tetraarylethanes. Interestingly, the presence of excess KOt-Bu generates the (E)-tetraarylethenes as the only product.

Supporting Information

Primary Data

 
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