Pd                         II                         -Catalyzed Enantioselective C(sp                         3                         )−H Activation/Cross-Coupling Reactions of Free Carboxylic Acids

Liang Hu; Peng Xiang Shen; Qian Shao; Kai Hong; Jennifer X. Qiao; Jin Quan Yu

doi:10.1002/anie.201813055

Pd ^II -Catalyzed Enantioselective C(sp ³ )−H Activation/Cross-Coupling Reactions of Free Carboxylic Acids

Liang Hu
, Peng Xiang Shen
, Qian Shao
, Kai Hong
, Jennifer X. Qiao
, Jin Quan Yu^*

^*Corresponding author for this work

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

143 Scopus citations

Abstract

Pd ^II -catalyzed enantioselective C(sp ³ )−H cross-coupling of free carboxylic acids with organoborons has been realized using either mono-protected amino acid (MPAA) ligands or mono-protected aminoethyl amine (MPAAM) ligands. A diverse range of aryl- and vinyl-boron reagents can be used as coupling partners to provide chiral carboxylic acids. This reaction provides an alternative approach to the enantioselective synthesis of cyclopropanecarboxylic acids and cyclobutanecarboxylic acids containing α-chiral tertiary and quaternary stereocenters. The utility of this reaction was further demonstrated by converting the carboxylic acid into cyclopropyl amine without loss of optical activity.

Original language	English
Pages (from-to)	2134-2138
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	58
Issue number	7
DOIs	https://doi.org/10.1002/anie.201813055
State	Published - 11 Feb 2019
Externally published	Yes

Keywords

C−H activation
arylation
palladium
vinylation

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10.1002/anie.201813055

Cite this

Hu, L., Shen, P. X., Shao, Q., Hong, K., Qiao, J. X., & Yu, J. Q. (2019). Pd ^II -Catalyzed Enantioselective C(sp ³ )−H Activation/Cross-Coupling Reactions of Free Carboxylic Acids Angewandte Chemie - International Edition, 58(7), 2134-2138. https://doi.org/10.1002/anie.201813055

Hu, Liang ; Shen, Peng Xiang ; Shao, Qian et al. / Pd ^II -Catalyzed Enantioselective C(sp ³ )−H Activation/Cross-Coupling Reactions of Free Carboxylic Acids In: Angewandte Chemie - International Edition. 2019 ; Vol. 58, No. 7. pp. 2134-2138.

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title = " Pd II -Catalyzed Enantioselective C(sp 3 )−H Activation/Cross-Coupling Reactions of Free Carboxylic Acids ",

abstract = " Pd II -catalyzed enantioselective C(sp 3 )−H cross-coupling of free carboxylic acids with organoborons has been realized using either mono-protected amino acid (MPAA) ligands or mono-protected aminoethyl amine (MPAAM) ligands. A diverse range of aryl- and vinyl-boron reagents can be used as coupling partners to provide chiral carboxylic acids. This reaction provides an alternative approach to the enantioselective synthesis of cyclopropanecarboxylic acids and cyclobutanecarboxylic acids containing α-chiral tertiary and quaternary stereocenters. The utility of this reaction was further demonstrated by converting the carboxylic acid into cyclopropyl amine without loss of optical activity.",

keywords = "C−H activation, arylation, palladium, vinylation",

author = "Liang Hu and Shen, \{Peng Xiang\} and Qian Shao and Kai Hong and Qiao, \{Jennifer X.\} and Yu, \{Jin Quan\}",

note = "Publisher Copyright: {\textcopyright} 2019 Wiley-VCH Verlag GmbH \& Co. KGaA, Weinheim",

year = "2019",

month = feb,

day = "11",

doi = "10.1002/anie.201813055",

language = "英语",

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Hu, L, Shen, PX, Shao, Q, Hong, K, Qiao, JX & Yu, JQ 2019, ' Pd ^II -Catalyzed Enantioselective C(sp ³ )−H Activation/Cross-Coupling Reactions of Free Carboxylic Acids ', Angewandte Chemie - International Edition, vol. 58, no. 7, pp. 2134-2138. https://doi.org/10.1002/anie.201813055

Pd ^II -Catalyzed Enantioselective C(sp ³ )−H Activation/Cross-Coupling Reactions of Free Carboxylic Acids . / Hu, Liang; Shen, Peng Xiang; Shao, Qian et al.
In: Angewandte Chemie - International Edition, Vol. 58, No. 7, 11.02.2019, p. 2134-2138.

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

TY - JOUR

T1 - Pd II -Catalyzed Enantioselective C(sp 3 )−H Activation/Cross-Coupling Reactions of Free Carboxylic Acids

AU - Hu, Liang

AU - Shen, Peng Xiang

AU - Shao, Qian

AU - Hong, Kai

AU - Qiao, Jennifer X.

AU - Yu, Jin Quan

PY - 2019/2/11

Y1 - 2019/2/11

N2 - Pd II -catalyzed enantioselective C(sp 3 )−H cross-coupling of free carboxylic acids with organoborons has been realized using either mono-protected amino acid (MPAA) ligands or mono-protected aminoethyl amine (MPAAM) ligands. A diverse range of aryl- and vinyl-boron reagents can be used as coupling partners to provide chiral carboxylic acids. This reaction provides an alternative approach to the enantioselective synthesis of cyclopropanecarboxylic acids and cyclobutanecarboxylic acids containing α-chiral tertiary and quaternary stereocenters. The utility of this reaction was further demonstrated by converting the carboxylic acid into cyclopropyl amine without loss of optical activity.

AB - Pd II -catalyzed enantioselective C(sp 3 )−H cross-coupling of free carboxylic acids with organoborons has been realized using either mono-protected amino acid (MPAA) ligands or mono-protected aminoethyl amine (MPAAM) ligands. A diverse range of aryl- and vinyl-boron reagents can be used as coupling partners to provide chiral carboxylic acids. This reaction provides an alternative approach to the enantioselective synthesis of cyclopropanecarboxylic acids and cyclobutanecarboxylic acids containing α-chiral tertiary and quaternary stereocenters. The utility of this reaction was further demonstrated by converting the carboxylic acid into cyclopropyl amine without loss of optical activity.

KW - C−H activation

KW - arylation

KW - palladium

KW - vinylation

UR - https://www.scopus.com/pages/publications/85060145107

U2 - 10.1002/anie.201813055

DO - 10.1002/anie.201813055

M3 - 文章

C2 - 30536546

AN - SCOPUS:85060145107

SN - 1433-7851

VL - 58

SP - 2134

EP - 2138

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 7

ER -

Hu L, Shen PX, Shao Q, Hong K, Qiao JX, Yu JQ. Pd ^II -Catalyzed Enantioselective C(sp ³ )−H Activation/Cross-Coupling Reactions of Free Carboxylic Acids Angewandte Chemie - International Edition. 2019 Feb 11;58(7):2134-2138. doi: 10.1002/anie.201813055

Pd ^II -Catalyzed Enantioselective C(sp ³ )−H Activation/Cross-Coupling Reactions of Free Carboxylic Acids

Abstract

Keywords

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