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Green and Selective Autocatalyzed Synthesis of Alcohols and Ketones
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Communication
Catalyst-Free Dehydrative α-Alkylation of Ketones with Alcohols: Green and Selective Autocatalyzed Synthesis of Alcohols and Ketones†
& & Prof. Dr. Qing Xu*,
& & Jianhui Chen,
& & Haiwen Tian,
& & Xueqin Yuan,
& & Shuangyan Li,
& & Chongkuan Zhou,
& & Dr. Jianping Liu
Article first published online: 24 NOV 2013
DOI: 10.1002/anie.
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Author Information
& & College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou, Zhejiang 325035 (China)
Email: Prof. Dr. Qing Xu ()
*College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou, Zhejiang 325035 (China)
& & †This research was supported by NNSFC (), SRF for ROCS of SEM, ZJNSF (Y4100579), and ZJQJTP (QJD0902004).
& & synthetic methods
Direct dehydrative α-alkylation reactions of ketones with alcohols are now realized under simple, practical, and green conditions without using external catalysts. These catalyst-free autocatalyzed alkylation methods can efficiently afford useful alkylated ketone or alcohol products in a one-pot manner and on a large scale by C[DOUBLE BOND]C bond formation of the in situ generated intermediates with subsequent controllable and selective Meerwein–Pondorf–Verley–Oppenauer-type redox processes.
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徐清，男，汉族，1977年11月出生，浙江永康人，中共党员、教授、博士、硕士研究生导师。1999年毕业于浙江大学化学系，获理学学士学位；同年保送浙江大学硕博连读研究生，于2004年6月获理学博士学位（导师：黄宪院士）；2004年10月赴日本产业技术综合研究所（National Institute of Advanced Industrial Science and Technology, AIST），作为特别研究员从事手性有机磷化合物的合成和应用研究（合作导师：Li-Biao Han教授）；2009年2月进入温州大学化学与材料工程学院从事教学科研工作；2012年12月破格晋升教授职称；入选浙江省高校优秀青年教师资助、温州市551人才第二层次；首届温州大学青年博士联谊会副会长，温州市青年联合会第八届委员会委员。研究方向为绿色化学和绿色合成研究、过渡金属催化反应研究、高选择元素有机化合物合成应用研究、不对称催化与合成研究，以及相关新反应机理研究。至今已在J. Am. Chem. Soc.、Angewan. Chem.、Green Chem.、Chem. Commun.、Org. Lett.、Adv. Synth. Catal.、J. Org. Chem.、Org. Biomol. Chem.、Mini-Rev. Med. Chem.、Synlett.、Tetrahedron Lett.、J. Organometallic Chem.等国际SCI学术期刊发表近四十篇学术论文，申请二十多项国内外发明专利、已授权两项；多篇论文被选为杂志封面论文、杂志年度优秀论文、浙江省基金优秀论文、温州市自然科学优秀论文，或被Science、Chem. Rev.、J. Am. Chem. Soc.、Angewan. Chem.、Green. Chem.等系列权威期刊重点引用或评价，或被Organic Chemistry Portal和Labome Org作为亮点收录介绍，或被研究同行和《化学工业日报》高度评价。研究成果获浙江省高校科优秀研成果奖、浙江省自然科学学术奖等。此外十多次受邀在大学和国际国内学术会议上作相关研究报告。
(1)& &Qing Xu,* Jianhui Chen, Haiwen Tian, Xueqin Yuan, Shuangyan Li, Chongkuan Zhou, Jianping Liu. Catalyst-Free Dehydrative α-Alkylation of Ketones with Alcohols: Green and Selective Autocatalyzed Synthesis of Alcohols and Ketones. Angewan. Chem. ;Angewan. Chem. Int. Ed.
(SCI-I, IF: 13.734)(2)& &Lei Yu,* Yulan Wu, Hongen Cao, Xu Zhang, Xinkang Shi, Jie Luan, Tian Chen, Yi Pan, and Qing Xu.* Facile Synthesis of 2-Methylenecyclobutanones via Ca(OH)2-Catalyzed Direct Condensation of Cyclobutanone with Aldehydes and (PhSe)2-Catalyzed Baeyer-Villiger Oxidation to 4-Methylenebutanolides. Green Chem. (SCI-II, IF: 6.828)(3)& & Erlei Zhang, Haiwen Tian, Sendong Xu, XiaochunYu, and Qing Xu.* Iron-Catalyzed Direct Synthesis of Imines from Amines or Alcohols and Amines via Aerobic Oxidative Reactions under Air. Org. Lett. 2013, 15 (11), . () (SCI-II, IF: 6.142) (4)& &Quan Liu, Zhongxiang Lu, Wenfei Ren, Kaibo Shen, Yu Wang, Qing Xu.* Efficient Synthesis of Unsymmetrical Heteroaryl Ethers by a Transition Metal-Free C-O Cross-Coupling Reaction of Activated and Unactivated Heteroaryl Chlorides with Alcohols and Phenols. Chin. J Chem. 2013, 31 (6), 764-772. () (SCI, IF: 0.917)(5)& &Bo Huang, Haiwen Tian, Shoushuai Lin, Meihua Xie, Xiaochun Yu,* Qing Xu.* Cu(I)/TEMPO-Catalyzed Aerobic Oxidative Synthesis of Imines Directly from Primary and Secondary Amines under Ambient and Neat Conditions. Tetrahedron Lett. 2013, 54 (22), . () (SCI-III, IF: 2.376)(6)& &Qing Xu,* Yong-Bo Zhou, Chang-Qiu Zhao, Shuang-Feng Yin, Li-Biao Han.* Transition Metal-Catalyzed Efficient and Green Transformations of P(O)−H Compounds to Functional Organophosphorus Compounds. Mini-Rev. Med. Chem. 2013, 13 (6), 824-835. () (SCI-III, IF: 2.865)(7)& &Qing Xu,* Jianhui Chen, Quan Liu. Aldehyde-Catalyzed Transition Metal-Free Dehydrative β-Alkylation of Methyl Carbinols with Alcohols. Adv. Synth. Catal. 2013, 355 (4), 697-704. () (SCI-II, IF: 5.535)(8)& &Lei Yu,* Yulan Wu, Tian Chen, Yi Pan, Qing Xu.* Direct Synthesis of Methylene-1,2-dichalcogenolanes via Radical [3+2] Cycloaddition of Methylenecyclopropanes with Elemental Chalcogens. Org. Lett. 2013, 15 (1), 144-147. () (SCI-II, IF: 6.142)(9)& &Qing Xu,* Qiang Li, Xiaogang Zhu, Jianhui Chen. Green and Scalable Aldehyde-Catalyzed Transition Metal-Free Dehydrative N-Alkylation of Amides and Amines with Alcohols. Adv. Synth. Catal. 2013, 355 (1), 73-80. ()(SCI-II, IF: 5.535) (被Organic Chemistry Portal摘录介绍：)(10) Qing Xu,* Qiang Li. Recent Advances of Transition Metal-Catalyzed Aerobic Dehydrative Reactions of Alcohols and Amines and Related Reactions. Chin. J. Org. Chem.2013, 33 (1), 18-35. () (SCI, IF: 0.741)(11) Haiwen Tian, Xiaochun Yu, Qiang Li, Jianxin Wang, Qing Xu.* General, Green, and Scalable Synthesis of Imines from Alcohols and Amines by a Mild and Efficient Copper-Catalyzed Aerobic Oxidative Reaction in Open Air at Room Temperature. Adv. Synth. Catal. 2012, 354 (14-15), .() (SCI-II, IF: 5.535)(12) Qing Xu, Chang-Qiu Zhao, Yong-Bo Zhou, Shuang-Feng Yin, Li-Biao Han.* Transition Metal-Catalyzed Transformations of P(O)-H Bonds. Chin. J. Org. Chem.2012, 32 (10), . () (SCI, IF: 0.741，外封面论文）(13) Xiaochun Yu, Lan Jiang, Qiang Li, Yuanyuan Xie, Qing Xu.* Palladium-Catalyzed N-Alkylation of Amides and Amines with Alcohols Employing the Aerobic Relay Race Methodology. Chin. J. Chem. 2012, 30 (10), . () (SCI, IF: 0.917)(14) Qiang Li, Songjian Fan, Qing Sun, Haiwen Tian, Xiaochun Yu, Qing Xu.* Copper-Catalyzed N-Alkylation of Amides and Amines with Alcohols Employing the Aerobic Relay Race Methodology. Org. Biomol. Chem.2012,10 (15), . () (SCI-III, IF: 3.568，外封面论文）(15) Shiheng Liao, Kangkang Yu, Qiang Li, Haiwen Tian, Zhengping Zhang, Xiaochun Yu, Qing Xu.* Copper-Catalyzed C-Alkylation of Secondary Alcohols and Methyl Ketones with Alcohols Employing the Aerobic Relay Race Methodology. Org. Biomol. Chem.2012, 10 (15), . () (SCI-III, IF: 3.568，外封面论文，同上）(16) Xiaochun Yu, Chuanzhi Liu, Lan Jiang, Qing Xu.* Manganese Dioxide Catalyzed N-Alkylation of Sulfonamides and Amines with Alcohols under Air. Org. Lett.2011, 13 (23), . () (SCI-II, IF: 6.142) (被Organic Chemistry Portal摘录介绍: )(17) Lan Jiang, Luolu Jin, Haiwen Tian, Xueqin Yuan, Xiaochun Yu,* Qing Xu.*Direct and Mild Palladium-Catalyzed Aerobic Oxidative Synthesis of Imines from Alcohols and Amines under Ambient Conditions. Chem. Commun. 2011, 47 (38), . () (SCI-II, IF: 6.378) (、)(18) Chuanzhi Liu, Shiheng Liao, Qiang Li, Sunlin Feng, Qing Sun, Xiaochun Yu,* Qing Xu.* Discovery and Mechanistic Studies of a General Air-Promoted Metal-Catalyzed Aerobic N-Alkylation Reaction of Amides and Amines with Alcohols. J. Org. Chem.2011, 76 (14), . () (SCI-II, IF: 4.564)(19) Sun Lin Feng, Chuan Zhi Liu, Qiang Li; Xiao Chun Yu, Qing Xu.*Rhodium-Catalyzed Aerobic N-Alkylation of Sulfonamides with Benzylic Alcohols. Chin. Chem. Lett.2011, 22 (9), . () (SCI, IF: 1.21) ()(20) Chuanzhi Liu, Xufeng Zang, Baohua Yu, Xiaochun Yu,* Qing Xu.* Microwave-Promoted TBAF-Catalyzed SNAr Reaction of Aryl Fluorides and ArSTMS: an Efficient Synthesis of Unsymmetrical Diaryl Thioethers. Synlett, 2011, (8), . () (SCI-III, IF: 2.655)(21) Qing Xu, Ruwei Shen, Yutaka Ono, Ritsuko Nagahata, Shigeru Shimada, Midori Goto, Li-Biao Han.* A New Oxapalladacycle Generated via Ortho C-H Activation of Phenylphosphinic Acid: Efficient Catalyst for Markovnikov-Type Additions of E-H Bonds to Alkynes. Chem. Commun. 2011, 47 (8), . () (SCI-II, IF: 6.378) (被Organic Chemistry Portal摘录介绍: ; 被Labome摘录介绍: )(22) Qing Xu, Han, Li-Biao.* Metal-catalyzed additions of H-P(O) bonds to carbon-carbon unsaturated bonds. J. Organometallic Chem.2011, 696 (1), 130-140. () (SCI, IF: 2.0)(23) Li-Biao Han,* Yutaka Ono, Qing Xu, Shigeru Shimada. Highly Selective Markovnikov-Type Addition of Hypervalent H-Spirophosphoranes to Alkynes Mediated by Palladium Acetate: Generality and Mechanism. Bull. Chem. Soc. Jpn. 2010, 83 (9), . () (SCI-III, IF: 1.436)(24) Qing Xu,* Li-Biao Han.* Transition Metal-Catalyzed Selective Hydrophosphorylation Reactions.(25) Gang Wang, Ruwei Shen, Qing Xu, Midori Goto, Yufen Zhao,* Li-Biao Han.* Stereospecific Coupling of H-Phosphinates and Secondary Phosphine Oxides with Amines and Alcohols: a General Method for the Preparation of Optically Active Organophosphorus Acid Derivatives. J. Org. Chem. 2010, 75 (11), . () (SCI-II, IF: 4.564)(26) Qing Xu, Chang-Qiu Zhao, Li-Biao Han.* Stereospecific Nucleophilic Substitution of Optically Pure H-Phosphinates: A General Way for the Preparation of Chiral P-Stereogenic Phosphine Oxides. J. Am. Chem. Soc. 2008, 130 (38), . () (SCI-I, IF: 10.677)(27) Qing Xu, Li-Biao Han.* Palladium-Catalyzed Asymmetric Hydrophosphorylation of Norbornenes. Org. Lett.2006, 8 (10), .( ) (SCI-II, IF: 6.142)(28) Qing Xu, Xian Huang,* Jingqi Yuan. Facile Synthesis of β-Organotellurobutenolides via Electrophilic Tellurolactonization of α-Allenoic Acids. J. Org. Chem.2005, 70 (17), . () (SCI-II, IF: 4.564)(29) Qing Xu, Xian Huang.* Cis-Carbocuperation of Acetylenic Sulfoxides and Corresponding Applications in the Regio- and Stereoselective Synthesis of Polysubstituted Vinyl Sulfoxides. Tetrahedron Lett.2004, 45 (29), . () (SCI-III, IF: 2.376)(30)
Qing Xu, Xian Huang,* Jun Ni. Hydrotelluration and Carbotelluration of Acetylenic Sulfoxides: Regio- and Stereoselective Preparation of α- and β-Organotellurovinyl Sulfoxides. Tetrahedron Lett. 2004, 45 (14), . () (SCI-III, IF: 2.376)(31) Xian Huang,* Chun-Gen Liang, Qing Xu, Qi-Wen He. Alkyne-Based, Highly Stereo- and Regioselective Synthesis of Stereodefined Fucntionalized Vinyl Tellurides. J. Org. Chem.2001, 66 (1), 74-80. () (SCI-II, IF: 4.564)代表论著
徐清*、吴华悦，《亨利反应(Henry Reaction)》（胡跃飞教授、林国强院士主编《现代有机反应》第七卷第三章, pp 93-155），化学工业出版社，2013年。主
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（1）& && && & 2013年2月，论文“Rhodium-Catalyzed Aerobic N-Alkylation of Sulfonamides with Benzylic Alcohols”(Chin. Chem. Lett.2011, 22 (9), )被评为。（2）& && & 2012年12月，《室温空气条件下直接温和的钯催化醇和胺有氧氧化合成亚胺的方法》获（排名1/4）。（3）& && & 2012年12月，《过渡金属催化醇与胺有氧反应机理研究及应用》获（排名1/2）。（4）& && & 2012年12月，入选首届。（5）& && & 2012年11月，入选。（6）& && & 2012年9月，论文“Direct and Mild Palladium-Catalyzed Aerobic Oxidative Synthesis of Imines from Alcohols and Amines under Ambient Conditions” (Chem. Commun. 2011, 47, 10833)被评为。优秀毕业生
优秀硕士毕业生：(1)& &10级硕士 田海雯（女）：发表 Adv. Synth. Catal.、Angewan. Chem.、Chem. Commun.、Org. Biomol. Chem.等论文；在校期间获10-11、11-12研究生一等奖学金，2012年研究生国家奖学金，2013年校级优秀毕业生、获华峰院长奖；考取复旦大学2013级博士研究生（导师：周锡庚教授）；(2)& &10级硕士 吴于兰（女，扬州大学13届毕业生，与俞磊副教授联合培养）：发表Org. Lett.、Green Chem. 等论文；2012年研究生国家奖学金；扬大化学化工学院优秀毕业生；江苏联环药业股份有限公司工作；(3)& &09级硕士 李强：发表 Adv. Synth. Catal.、Org. Biomol. Chem.、J. Org. Chem.等论文；考取湖南大学12级博士研究生（导师：韩立彪教授）；(4)& &09级硕士 姜澜（女）：发表 Chem. Commun.、Org. Lett.等论文；衢州巨化集团工作；优秀本科毕业生：(1)& &06级本科生 臧旭峰：本课题组10届本科毕业论文学生，期间发表Synlett、J. Chem. Res.等论文；在校期间多次获得一等、二等奖学金、三好学生、优秀学生干部、优秀学生党务干部、校优秀毕业生等荣誉称号；考取华南理工大学10级硕士研究生，现转攻读博士研究生（导师：曹德榕教授）；(2)& &06级本科生 邵羽裳（女）：本课题组10届本科毕业论文学生；考取华东师范大学10级硕士研究生（导师：李艳忠教授）；(3)& &06级本科生 谢建江：本课题组10届本科毕业论文学生；在校期间多次获得奖学金；考取南京理工大学10级硕士研究生（导师：李峰副教授）；现就职于三门核电有限公司；(4)& &08级本科生 崔巍：本课题组12届本科毕业论文学生；考取华南理工大学12级硕士研究生（导师：曹德榕教授）；(5)& &08级本科生 周勇：本课题组12届本科毕业论文学生；2011年国家励志奖学金、12级华东理工大学和上海有机所联合培养硕士研究生（导师：游书力研究员）；(6)& &08级本科生 汪家宏：本课题组12届本科毕业论文学生；2011年国家励志奖学金、考取华东理工大学12级硕士研究生；(7)& &08级本科生 张俊：本课题组12届本科毕业论文学生；考取华东师范大学12级硕士研究生；(8)& &09级本科生 罗明部：本课题组13届本科毕业论文学生；考取福州大学13级硕士研究生；联系方式
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