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Literature Report Reporter: Ben Rong Advisor: Prof. Zhao Jing 13/07/20

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Page 1: Literature Report - pkusz.edu.cnweb.pkusz.edu.cn/zhao/files/2013/05/Rhodium-Catalyzed-Intermolec… · Catalytic C-H bond Activation for Direct C-C, C-O and C-N bond Formation Prof

Literature Report

Reporter: Ben Rong Advisor: Prof. Zhao Jing 13/07/20

Page 2: Literature Report - pkusz.edu.cnweb.pkusz.edu.cn/zhao/files/2013/05/Rhodium-Catalyzed-Intermolec… · Catalytic C-H bond Activation for Direct C-C, C-O and C-N bond Formation Prof

Prof. Sukbok Chang’s Profile

Education: B.S. : Korea University Ph.D. : Harvard University ( Advisor: Prof. Eric. N. Jacobsen ) Postdoc. : California Institute of Technology ( Advisor: Prof. Robert H. Grubbs )

Research Interests: Catalytic C-H bond Activation for Direct C-C, C-O and C-N bond Formation

Prof. Sukbok Chang, Korea Advanced

Institute Science and Technology ( KAIST )

Page 3: Literature Report - pkusz.edu.cnweb.pkusz.edu.cn/zhao/files/2013/05/Rhodium-Catalyzed-Intermolec… · Catalytic C-H bond Activation for Direct C-C, C-O and C-N bond Formation Prof

Rhodium-Catalyzed Intermolecular Amidation of Arenes with

Sulfonyl Azides

Ji Young Kim,† Sae Hume Park,† Jaeyune Ryu, Seung Hwan Cho, Seok Hwan Kim, and Sukbok Chang*

J. Am. Chem. Soc. 2012, 134, 9110 − 9113

Page 4: Literature Report - pkusz.edu.cnweb.pkusz.edu.cn/zhao/files/2013/05/Rhodium-Catalyzed-Intermolec… · Catalytic C-H bond Activation for Direct C-C, C-O and C-N bond Formation Prof

Introduction C−N Bond Formation Routes to Aryl Amine

Page 5: Literature Report - pkusz.edu.cnweb.pkusz.edu.cn/zhao/files/2013/05/Rhodium-Catalyzed-Intermolec… · Catalytic C-H bond Activation for Direct C-C, C-O and C-N bond Formation Prof

Condition Optimization

Page 6: Literature Report - pkusz.edu.cnweb.pkusz.edu.cn/zhao/files/2013/05/Rhodium-Catalyzed-Intermolec… · Catalytic C-H bond Activation for Direct C-C, C-O and C-N bond Formation Prof

Condition Optimization

Page 7: Literature Report - pkusz.edu.cnweb.pkusz.edu.cn/zhao/files/2013/05/Rhodium-Catalyzed-Intermolec… · Catalytic C-H bond Activation for Direct C-C, C-O and C-N bond Formation Prof

Substrate Scope 2-Phenylpyridine Derivatives

Page 8: Literature Report - pkusz.edu.cnweb.pkusz.edu.cn/zhao/files/2013/05/Rhodium-Catalyzed-Intermolec… · Catalytic C-H bond Activation for Direct C-C, C-O and C-N bond Formation Prof

Substrate Scope 2-Phenylpyridine Derivatives

Page 9: Literature Report - pkusz.edu.cnweb.pkusz.edu.cn/zhao/files/2013/05/Rhodium-Catalyzed-Intermolec… · Catalytic C-H bond Activation for Direct C-C, C-O and C-N bond Formation Prof

Substrate Scope Sulfonyl Azides

Page 10: Literature Report - pkusz.edu.cnweb.pkusz.edu.cn/zhao/files/2013/05/Rhodium-Catalyzed-Intermolec… · Catalytic C-H bond Activation for Direct C-C, C-O and C-N bond Formation Prof

Proposed Reaction Pathway

Page 11: Literature Report - pkusz.edu.cnweb.pkusz.edu.cn/zhao/files/2013/05/Rhodium-Catalyzed-Intermolec… · Catalytic C-H bond Activation for Direct C-C, C-O and C-N bond Formation Prof

Rhodium-Catalyzed Direct C-H Amination of Benzamides with Aryl

Azides

Jaeyune Ryu, Kwangmin Shin, Sae Hume Park, Ji Young Kim, and Sukbok Chang*

Angew. Chem. Int. Ed. 2012 , 51 , 9904 –9908

Page 12: Literature Report - pkusz.edu.cnweb.pkusz.edu.cn/zhao/files/2013/05/Rhodium-Catalyzed-Intermolec… · Catalytic C-H bond Activation for Direct C-C, C-O and C-N bond Formation Prof

Introduction

Page 13: Literature Report - pkusz.edu.cnweb.pkusz.edu.cn/zhao/files/2013/05/Rhodium-Catalyzed-Intermolec… · Catalytic C-H bond Activation for Direct C-C, C-O and C-N bond Formation Prof

Optimization of Directing Group

Page 14: Literature Report - pkusz.edu.cnweb.pkusz.edu.cn/zhao/files/2013/05/Rhodium-Catalyzed-Intermolec… · Catalytic C-H bond Activation for Direct C-C, C-O and C-N bond Formation Prof

Substrate Scope Aromatic amides

Page 15: Literature Report - pkusz.edu.cnweb.pkusz.edu.cn/zhao/files/2013/05/Rhodium-Catalyzed-Intermolec… · Catalytic C-H bond Activation for Direct C-C, C-O and C-N bond Formation Prof

Substrate Scope Aryl azides

Page 16: Literature Report - pkusz.edu.cnweb.pkusz.edu.cn/zhao/files/2013/05/Rhodium-Catalyzed-Intermolec… · Catalytic C-H bond Activation for Direct C-C, C-O and C-N bond Formation Prof

Substrate Scope Aromatic Ketoximes

Page 17: Literature Report - pkusz.edu.cnweb.pkusz.edu.cn/zhao/files/2013/05/Rhodium-Catalyzed-Intermolec… · Catalytic C-H bond Activation for Direct C-C, C-O and C-N bond Formation Prof

Proposed Reaction Pathway

Page 18: Literature Report - pkusz.edu.cnweb.pkusz.edu.cn/zhao/files/2013/05/Rhodium-Catalyzed-Intermolec… · Catalytic C-H bond Activation for Direct C-C, C-O and C-N bond Formation Prof

Thank you for your attention!