Chemoselective Carbophilic Addition of α-Diazoesters through Ligand-Controlled Gold Catalysis†
Yumeng Xi
C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, WV 26506 (USA) http://community.wvu.edu/∼xs007/
These authors contributed equally to this work.
Search for more papers by this authorYijin Su
C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, WV 26506 (USA) http://community.wvu.edu/∼xs007/
These authors contributed equally to this work.
Search for more papers by this authorZhaoyuan Yu
School of Chemistry and Chemical Engineering, Chongqing University, 400030, Chongqing (P.R. China)
Search for more papers by this authorBoliang Dong
C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, WV 26506 (USA) http://community.wvu.edu/∼xs007/
Search for more papers by this authorEdward J. McClain
C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, WV 26506 (USA) http://community.wvu.edu/∼xs007/
Search for more papers by this authorCorresponding Author
Prof. Yu Lan
School of Chemistry and Chemical Engineering, Chongqing University, 400030, Chongqing (P.R. China)
Yu Lan, School of Chemistry and Chemical Engineering, Chongqing University, 400030, Chongqing (P.R. China)
Xiaodong Shi, C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, WV 26506 (USA) http://community.wvu.edu/∼xs007/
Search for more papers by this authorCorresponding Author
Prof. Xiaodong Shi
C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, WV 26506 (USA) http://community.wvu.edu/∼xs007/
Yu Lan, School of Chemistry and Chemical Engineering, Chongqing University, 400030, Chongqing (P.R. China)
Xiaodong Shi, C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, WV 26506 (USA) http://community.wvu.edu/∼xs007/
Search for more papers by this authorYumeng Xi
C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, WV 26506 (USA) http://community.wvu.edu/∼xs007/
These authors contributed equally to this work.
Search for more papers by this authorYijin Su
C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, WV 26506 (USA) http://community.wvu.edu/∼xs007/
These authors contributed equally to this work.
Search for more papers by this authorZhaoyuan Yu
School of Chemistry and Chemical Engineering, Chongqing University, 400030, Chongqing (P.R. China)
Search for more papers by this authorBoliang Dong
C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, WV 26506 (USA) http://community.wvu.edu/∼xs007/
Search for more papers by this authorEdward J. McClain
C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, WV 26506 (USA) http://community.wvu.edu/∼xs007/
Search for more papers by this authorCorresponding Author
Prof. Yu Lan
School of Chemistry and Chemical Engineering, Chongqing University, 400030, Chongqing (P.R. China)
Yu Lan, School of Chemistry and Chemical Engineering, Chongqing University, 400030, Chongqing (P.R. China)
Xiaodong Shi, C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, WV 26506 (USA) http://community.wvu.edu/∼xs007/
Search for more papers by this authorCorresponding Author
Prof. Xiaodong Shi
C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, WV 26506 (USA) http://community.wvu.edu/∼xs007/
Yu Lan, School of Chemistry and Chemical Engineering, Chongqing University, 400030, Chongqing (P.R. China)
Xiaodong Shi, C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, WV 26506 (USA) http://community.wvu.edu/∼xs007/
Search for more papers by this authorWe are grateful to the NSF (CAREER-CHE-0844602 and CHE-1228336) and the NSFC (No. 21228204) for financial support. Y.L. acknowledges support from the National Science Foundation of China (No. 21372266 and 51302327).
Graphical Abstract
Carbocation or carbene? The chemoselective addition of arenes and 1,3-diketones to α-aryldiazoesters was achieved through ligand-controlled gold catalysis. The gold catalyst with electron-deficient phosphite as the ancillary ligand exclusively gave the carbophilic addition products, thus representing a new and efficient approach to form “carbophilic carbocations”, which selectively react with carbon nucleophiles.
Abstract
The chemoselective addition of arenes and 1,3-diketones to α-aryldiazoesters was achieved through ligand-controlled gold catalysis. Unlike a dirhodium catalyst (which promotes C
H insertion and cyclopropanation) and a copper catalyst (which catalyzes OH and NH insertions), the gold catalyst with an electron-deficient phosphite as the ancillary ligand exclusively gave the carbophilic addition product, thus representing a new and efficient approach to form “carbophilic carbocations”, which selectively react with carbon nucleophiles.
Supporting Information
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