Synthesis 2018; 50(22): 4429-4434
DOI: 10.1055/s-0037-1610158
paper
© Georg Thieme Verlag Stuttgart · New York

Modular Dihydrobenzoazaphosphole Ligands for Suzuki–Miyaura Cross-Coupling

a  Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, Ridgefield, CT 06877, USA   Email: yongda.zhang@boehringer-ingelheim.com   Email: chris.senanayake@boehringer-ingelheim.com
,
Kendricks S. Lao
a  Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, Ridgefield, CT 06877, USA   Email: yongda.zhang@boehringer-ingelheim.com   Email: chris.senanayake@boehringer-ingelheim.com
,
Joshua D. Sieber
a  Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, Ridgefield, CT 06877, USA   Email: yongda.zhang@boehringer-ingelheim.com   Email: chris.senanayake@boehringer-ingelheim.com
,
Yibo Xu
a  Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, Ridgefield, CT 06877, USA   Email: yongda.zhang@boehringer-ingelheim.com   Email: chris.senanayake@boehringer-ingelheim.com
,
Linglin Wu
a  Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, Ridgefield, CT 06877, USA   Email: yongda.zhang@boehringer-ingelheim.com   Email: chris.senanayake@boehringer-ingelheim.com
,
Xiao-Jun Wang
a  Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, Ridgefield, CT 06877, USA   Email: yongda.zhang@boehringer-ingelheim.com   Email: chris.senanayake@boehringer-ingelheim.com
,
Jean-Nicolas Desrosiers
a  Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, Ridgefield, CT 06877, USA   Email: yongda.zhang@boehringer-ingelheim.com   Email: chris.senanayake@boehringer-ingelheim.com
,
Heewon Lee
a  Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, Ridgefield, CT 06877, USA   Email: yongda.zhang@boehringer-ingelheim.com   Email: chris.senanayake@boehringer-ingelheim.com
,
a  Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, Ridgefield, CT 06877, USA   Email: yongda.zhang@boehringer-ingelheim.com   Email: chris.senanayake@boehringer-ingelheim.com
,
Zhengxu S. Han
a  Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, Ridgefield, CT 06877, USA   Email: yongda.zhang@boehringer-ingelheim.com   Email: chris.senanayake@boehringer-ingelheim.com
,
Nathan K. Yee
a  Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, Ridgefield, CT 06877, USA   Email: yongda.zhang@boehringer-ingelheim.com   Email: chris.senanayake@boehringer-ingelheim.com
,
Jinhua J. Song
a  Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, Ridgefield, CT 06877, USA   Email: yongda.zhang@boehringer-ingelheim.com   Email: chris.senanayake@boehringer-ingelheim.com
,
Amy R. Howell
b  Department of Chemistry, University of Connecticut, Storrs, CT 06269, USA
,
Chris H. Senanayake*
a  Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, Ridgefield, CT 06877, USA   Email: yongda.zhang@boehringer-ingelheim.com   Email: chris.senanayake@boehringer-ingelheim.com
› Author Affiliations
Further Information

Publication History

Received: 13 March 2018

Accepted after revision: 24 April 2018

Publication Date:
12 June 2018 (eFirst)

Dedicated to Professor Scott E. Denmark on the occasion of his 65th birthday

Published as part of the Special Section dedicated to Scott E. Denmark on the occasion of his 65th birthday

Abstract

A new family of dihydrobenzoazaphosphosphole ligands was prepared and shown to enable modification of the phosphine electronic character by variation of the N-substituent. This new family of phosphines was shown to be highly active in the Pd-catalyzed Suzuki–Miyaura cross-coupling reaction with hindered coupling partners.

Supporting Information

 
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