Transition-metal-free C(sp 2)–C(sp 3) cross-coupling of α-(pseudo)halo aliphatic ketones with boronic acids via a 1,4-metallate shift - Details

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Suzuki-type　cross-coupling　is　one　of　the　most　common　strategies　for　the　construction　of　C–C　bonds.　Despite　great　progress　on　the　preparation　of　C(sp　2)–C(sp　2)　bonds,　C(sp　2)–C(sp　3)　cross-coupling　with　aliphatic　halides　remains　rare,　especially　with　tertiary　aliphatic　halides　and　under　transition-metal-free　conditions.　Here　we　report　an　efficient　C(sp　2)–C(sp　3)　cross-coupling　between　α-(pseudo)halo　aliphatic　ketones　and　arylboronic　acids　via　a　1,4-metallate　shift.　The　α-arylated　ketones　obtained　from　this　protocol　under　transition-metal-free　and　additive-free　conditions　in　the　presence　of　base　are　formed　when　the　key　intermediate　enolate　traps　the　arylboronic　acid,　leading　to　a　tetracoordinate　boron　intermediate.　A　subsequent　1,4-metallate　shift　affords　the　Suzuki-type　coupling　products.　This　strategy　provides　a　practical,　scalable　and　operationally　straightforward　method　for　the　synthesis　of　C(sp　2)–C(sp　3)　bonds,　and　is　compatible　with　challenging　tertiary　aliphatic　halides,　allowing　for　the　preparation　of　1,3-disubstituted　target　products.　[Figure　not　available:　see　fulltext.].　©　2023,　The　Author(s),　under　exclusive　licence　to　Springer　Nature　Limited.

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[ 1 ] [Li X.]Institute of Next Generation Matter Transformation, College of Material Sciences Engineering, Huaqiao University, Xiamen, China
[ 2 ] [Chen H.]School of Chemistry and Chemical Engineering, State Key Laboratory of Antiviral Drugs, Henan Normal University, Xinxiang, China
[ 3 ] [Wang H.]Institute of Next Generation Matter Transformation, College of Material Sciences Engineering, Huaqiao University, Xiamen, China
[ 4 ] [Zhang Q.]Institute of Next Generation Matter Transformation, College of Material Sciences Engineering, Huaqiao University, Xiamen, China
[ 5 ] [Sheng H.]Institute of Next Generation Matter Transformation, College of Material Sciences Engineering, Huaqiao University, Xiamen, China
[ 6 ] [Lan Y.]School of Chemistry and Chemical Engineering, State Key Laboratory of Antiviral Drugs, Henan Normal University, Xinxiang, China
[ 7 ] [Lan Y.]Chongqing Key Laboratory of Theoretical and Computational Chemistry, School of Chemistry and Chemical Engineering, Chongqing University, Chongqing, China
[ 8 ] [Lan Y.]College of Chemistry and Institute of Green Catalysis, Zhengzhou University, Zhengzhou, China
[ 9 ] [Song Q.]Institute of Next Generation Matter Transformation, College of Material Sciences Engineering, Huaqiao University, Xiamen, China
[ 10 ] [Song Q.]School of Chemistry and Chemical Engineering, State Key Laboratory of Antiviral Drugs, Henan Normal University, Xinxiang, China
[ 11 ] [Song Q.]Key Laboratory of Molecule Synthesis and Function Discovery, Fujian Province University, College of Chemistry at Fuzhou University, Fuzhou, China

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Transition-metal-free C(sp2)-C(sp3) cross-coupling of α-(pseudo)halo aliphatic ketones with boronic acids via a 1,4-metallate shift
2023，NATURE SYNTHESIS

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Nature Synthesis

ISSN： 2731-0582

Year： 2023

Issue： 12

Volume： 2

Page： 1211-1221

1 7 . 5

JCR@2023

1 7 . 5 0 0

JCR@2023

JCR Journal Grade：1

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SCOPUS Cited Count： 12

ESI Highly Cited Papers on the List： 0 Unfold All

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30 Days PV： 3

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