Palladium-Catalyzed Atroposelective Kinetic C−H Olefination and Allylation for the Synthesis of C−B Axial Chirality - Details

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Abstract：

The　direct　C−H　functionalization　of　1,2-benzazaborines,　especially　asymmetric　version,　remains　a　great　challenge.　Here　we　report　a　palladium-catalyzed　enantioselective　C−H　olefination　and　allylation　reactions　of　1,2-benzazaborines.　This　asymmetric　approach　is　a　kinetic　resolution　(KR),　providing　various　C−B　axially　chiral　2-aryl-1,2-benzazaborines　and　3-substituted　2-aryl-1,2-benzazaborines　in　generally　high　yields　with　excellent　enantioselectivities　(selectivity　(S)　factor　up　to　354).　The　synthetic　potential　of　this　reaction　is　showcased　by　late-stage　modification　of　complex　molecules,　scale-up　reaction,　and　applications.　©　2023　Wiley-VCH　GmbH.

Keyword：

Allylation Catalysis Chirality Enantioselectivity Kinetics Palladium Stereochemistry

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[ 1 ] [Xu, Jie]Key Laboratory of Molecule Synthesis and Function Discovery, Fujian Province University, College of Chemistry at Fuzhou University, Fujian, Fuzhou; 350108, China
[ 2 ] [Qiu, Weihua]Key Laboratory of Molecule Synthesis and Function Discovery, Fujian Province University, College of Chemistry at Fuzhou University, Fujian, Fuzhou; 350108, China
[ 3 ] [Zhang, Xu]Key Laboratory of Molecule Synthesis and Function Discovery, Fujian Province University, College of Chemistry at Fuzhou University, Fujian, Fuzhou; 350108, China
[ 4 ] [Wu, Zhihan]Key Laboratory of Molecule Synthesis and Function Discovery, Fujian Province University, College of Chemistry at Fuzhou University, Fujian, Fuzhou; 350108, China
[ 5 ] [Zhang, Zhen]Key Laboratory of Molecule Synthesis and Function Discovery, Fujian Province University, College of Chemistry at Fuzhou University, Fujian, Fuzhou; 350108, China
[ 6 ] [Yang, Kai]Key Laboratory of Molecule Synthesis and Function Discovery, Fujian Province University, College of Chemistry at Fuzhou University, Fujian, Fuzhou; 350108, China
[ 7 ] [Song, Qiuling]Key Laboratory of Molecule Synthesis and Function Discovery, Fujian Province University, College of Chemistry at Fuzhou University, Fujian, Fuzhou; 350108, China
[ 8 ] [Song, Qiuling]School of Chemistry and Chemical Engineering, Henan Normal University, Henan, Xinxiang; 453007, China

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Source ：

Angewandte Chemie - International Edition

ISSN： 1433-7851

Year： 2023

Issue： 47

Volume： 62

1 6 . 1

JCR@2023

1 6 . 1 0 0

JCR@2023

JCR Journal Grade：1

CAS Journal Grade：1

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ESI Highly Cited Papers on the List： 0 Unfold All

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30 Days PV： 2

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