NiH-Catalyzed Reductive Relay Hydroalkylation: A Strategy for the Remote C(sp3)−H Alkylation of Alkenes
Fang Zhou
State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093 China
Search for more papers by this authorJin Zhu
State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093 China
Search for more papers by this authorYao Zhang
State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093 China
Search for more papers by this authorCorresponding Author
Prof. Shaolin Zhu
State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093 China
Search for more papers by this authorFang Zhou
State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093 China
Search for more papers by this authorJin Zhu
State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093 China
Search for more papers by this authorYao Zhang
State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093 China
Search for more papers by this authorCorresponding Author
Prof. Shaolin Zhu
State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093 China
Search for more papers by this authorDedicated to Professor David W. C. MacMillan on the occasion of his 50th birthday
Graphical Abstract
The synergistic combination of chain walking, a process involving repeated migratory insertions and β-H eliminations, and cross-coupling chemistry led to the development of a mild, efficient NiH-catalyzed process for the remote hydroalkylation of alkenes. Unfunctionalized C(sp3)−C(sp3) bonds were constructed from two simple feedstock chemicals, namely olefins and alkyl halides.
Abstract
The terminal-selective, remote C(sp3)−H alkylation of alkenes was achieved by a relay process combining NiH-catalyzed hydrometalation, chain walking, and alkylation. This method enables the construction of unfunctionalized C(sp3)−C(sp3) bonds under mild conditions from two simple feedstock chemicals, namely olefins and alkyl halides. The practical value of this transformation is further demonstrated by the large-scale and regioconvergent alkylation of isomeric mixtures of olefins at low catalyst loadings.
Supporting Information
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