烯酸加成酯化反应催化剂研究进展
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摘要
烯烃与羧酸在催化剂作用下进行加成反应生成羧酸酯,这一反应属于原子经济反应,越来越受到研究者的关注。综述21世纪以来烯烃与羧酸加成酯化反应催化剂的研究进展,包括磺酸类催化剂、离子交换树脂催化剂、杂多酸化合物催化剂、离子液体催化剂、沸石分子筛催化剂和过渡金属化合物催化剂等,对各类催化剂活性进行比较,并展望烯酸加成酯化反应催化剂的研究方向。
The esterification of carboxylic acid and olefin which is an atom economic reaction with 100%atom efficiency has attracted extensive attentions across academic and industrial communities. The research progress on catalysts for esterification of carboxylic acid and olefin was reviewed since 21 stcentury including sulfonic acid based catalysts,ion exchange resin,heteropolyacid,ionic liquid,zeolite,transition metal compounds and so on. Catalytic performances of catalysts were compared and the research directions of catalysts used for esterification of carboxylic acid and olefin were also proposed.
The esterification of carboxylic acid and olefin which is an atom economic reaction with 100%atom efficiency has attracted extensive attentions across academic and industrial communities. The research progress on catalysts for esterification of carboxylic acid and olefin was reviewed since 21 stcentury including sulfonic acid based catalysts,ion exchange resin,heteropolyacid,ionic liquid,zeolite,transition metal compounds and so on. Catalytic performances of catalysts were compared and the research directions of catalysts used for esterification of carboxylic acid and olefin were also proposed.
引文
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[5]Wang Bo,Gu Yanlong,Yang Liming,et al. Sulfamic acid as a green,efficient,recyclable and reusable catalyst for direct addition of aliphatic acid with cyclic olefins[J]. Catalysis Letters,2004,96:71-74.
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[8]Zhou Feng,Tang Jihai,Fei Zhaoyang,et al. Efficient cyclohexyl acrylate production by direct addition of acrylic acid and cyclohexene over SBA-15-SO3H[J]. Journal of Porous Materials,2014,21:149-155.
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[11]Zheng Huidong,Yan Zhongyi,Chu Shijiao,et al. Continuous synthesis of isobornyl acetate catalyzed by a strong acid cation exchange resin in an oscillatory flow reactor[J].Chemical Engineering&Processing:Process Intensification,2018,134:1-8.
[12]杨焕欣,杜长海,朱敏亮,等.阳离子交换树脂催化1-丁烯合成醋酸仲丁酯[J].化学工程师,2009,12:4-6.Yang Huanxin,Du Changhai,Zhu Minliang,et al. Synthesis of sec-butyl acetate catalyzed by strong acid cation exchange resin[J]. Chemical Engineer,2009,12:4-6.
[13]朱敏亮,徐平,杜长海.改性离子交换树脂催化合成醋酸仲丁酯[J].化学工程师,2007,3:13-15.Zhu Minliang,Xu Ping,Du Changhai. Synthesis of secbutyl acetate catalyzed by modified strong acid cation ion exchange resin[J]. Chemical Engineer,2007,3:13-15.
[14]许燕,汤吉海,崔咪芬,等.树脂催化甲基丙烯酸与环己烯反应合成甲基丙烯酸环己酯[J].石油化工,2011,40(10):1042-1045.Xu Yan,Tang Jihai,Cui Mifen,et al. Synthesis of cyclohexyl methacrylate from methacrylic acid and cyclohexene over resin catalyst synthesis of cyclohexyl methacrylate from methacrylic acid and cyclohexene over resin catalyst[J].Petrochemical Technology,2011,40(10):1042-1045.
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[17]Alexandre Demolis,Marion Eternot,Nadine Essayem,et al.New insights into the reactivity of biomass with butenes for the synthesis of butyl levulinates[J]. Chem Sus Chem,2017,10:2612-2617.
[18]Zhang Zhijun,Wang Qingwen,Yang Xulai,et al. Sulfonic acid resin-catalyzed addition of phenols,carboxylic acids,and water to olefins:model reactions for catalytic upgrading of bio-oil[J]. Bioresource Technology,2010,101:3685-3695.
[19]高文艺.磷铝杂原子固体酸催化剂催化合成乙酸异丙酯[J].精细石油化工进展,2003,4(12):30-31.Gao Wenyi. Catalytic Synthesis of isopropyl acetate using heteroatom-containing aluminophosphate solid acid catalyst[J]. Advances in Fine Petrochemicals,2003,4(12):30-31.
[20]王莉,魏民. Cs2. 5H0. 5PW12O40/Si O2催化剂上乙酸与烯烃酯化反应研究[J].化学与黏合,2006,28(2):94-96.Wang Li,Wei Min. Esterification of acetic acid and olefin over Cs2. 5H0. 5PW12O40/Si O2catalyst[J] Chemistry and Adhesion,2006,28(2):94-96.
[21]宋旭春,李萍,张起凯,等.固载杂多酸催化丁烯-1与乙酸合成乙酸丁酯[J].抚顺石油学院学报,2001,21(1):8-11.Song Xuchun,Li Ping,Zhang Qikai,et al. Synthesis ofbutyl acetate catalyzed by heteropolyacid catalyst supported on activated carbon[J]. Journal of Fushun Petroleum Institute,2001,21(1):8-11.
[22]杜长海,刘莹红,宋蓓蓓,等.磷钨酸催化混合C4合成醋酸仲丁酯[J].精细化工,2009,26(4):376-379.Du Changha,Liu Yinghong,Song Beibei,et al. Synthesis of sec-butyl acetate from mixed C4using the catalyst of phosphotungstic acid[J]. Fine Chemical,2009,26(4):376-379.
[23]徐平,金冲,杜长海.磷钨杂多酸催化合成醋酸仲丁酯[J].化学与生物工程,2007,24(12):22-24.Xu Ping,Jin Chong,Du Changhai. Synthesis of sec-butylacetate catalyzed by 12-tungst rophosphoric acid[J].Chemistry&Bioengineering,2007,24(12):22-24.
[24]李琴,柳云骐,周永敏,等.负载型杂多酸催化2-丁烯与醋酸直接酯化[J].石油化工,2007,36(12):1220-1224.Li Qin,Liu Yunqi,Zhou Yongmin,et al. Esterification of2-butylene with acetic acid catalyzed by silica-supported heteropolyacid[J]. Petrochemical Technology,2007,36(12):1220-1224.
[25]de Meireles Augusto L P,da Silva Rocha Kelly A,Ivan V Kozhevnikov,et al. Esterification of camphene over heterogeneous heteropoly acid catalysts:synthesis of isobornyl carboxylates[J]. Applied Catalysis A:General,2011,409-410:82-86.
[26]Robles-Dutenhefner Patricia A,da Silva Kelly A,Siddiqui M Rafiq H,et al. Hydration and acetoxylation of monoterpenes catalyzed by heteropoly acid[J]. Journal of Molecular Catalysis A:Chemical,2001,175:33-42.
[27]Yamamoto Yoshimi,Hatanaka Shigeru,Tsuji Katsuyuki,et al. Direct addition of acetic acid to ethylene to form ethyl acetate in the presence of H4Si W12O40/Si O2[J]. Applied Catalysis A:General,2008,344:55-60.
[28]Gu Yanlong,Shi Feng,Deng Youquan. Esterification of aliphatic acids with olefin promoted by Brnsted acidic ionic liquids[J]. Journal of Molecular Catalysis A:Chemical,2004,212:71-75.
[29]Duan Zhiying,Gu Yanlong,Zhang Juan,et al. Protic pyridinium ionic liquids:synthesis,acidity determination and their performances for acid catalysis[J]. Journal of Molecular Catalysis A:Chemical,2006,250:163-168.
[30]Liu Shiwei,Xie Congxia,Yu Shitao,et al. Esterification ofα-pinene and acetic acid using acidic ionic liquids as catalysts[J]. Catalysis Communications,2008,9:1634-1638.
[31]Gainsford Graeme J,Hosie Camila F,Weston Roderick J.Conversion ofα-pinene to terpinyl acetate over H-beta zeolites[J]. Applied Catalysis A:General,2001,209(1/2):269-277.
[32]Castanheiro J E,Fonseca I M,Ramos A M,et al. Acetoxylation of camphene catalysed by beta zeolite[J]. Catalysis Communications,2008,9:2205-2208.
[33]Yadav Mukesh Kr,Patil Mallikarjun V,Jasra Raksh V.Acetoxylation and hydration of limonene andα-pinene using cation-exchanged zeolite beta[J]. Journal of Molecular Catalysis A:Chemical,2009,297:101-109.
[34]Horiuchi C,Fukushima Tomoaki,Furuta Noriyuki,et al.Esterification of alkene with cerium(Ⅳ)sulfate in carboxylic acid[J]. Journal of Chemical Research,2003,(S):270-272.
[35]Essayem N,Martin V,Riondel A,et al. Esterification of acrylic acid with but-1-ene over sulfated Fe-and Mn-promoted zirconia[J]. Applied Catalysis A:General,2007,326:74-81.
[36]Yang Caiguang,He Chuan. Gold(Ⅰ)-catalyzed intermolecular addition of phenols and carboxylic acids to olefins[J]. Journal of the American Chemical Society,2005,127(19):6966-6967.
[37]Li Zigang,Zhang Junliang,Brouwer Chad,et al. Brnsted acid catalyzed addition of phenols,carboxylic acids,and tosylamides to simple olefins[J]. Organic Letters,2006,8(19):4175-4178.
[38]Yang Caiguang,Reich Nicholas W,Shi Zhangjie,et al.Intramolecular Additions of alcohols and carboxylic acids to inert olefins catalyzed by silver(Ⅰ)triflate[J]. Organic Letters,2005,7(21):4553-4556.
[39]Adrio Luis A,Quek Louisa Shuyi,Taylor Jason G,et al.Copper-catalysed intramolecular O-H addition to unactivated alkenes[J]. Tetrahedron,2009,65:10334-10338.
[40]Weiwer Michel,Dunach Elisabet. Indium(Ⅲ)-catalysed highly regioselective addition of thiolacetic acid to non-activated olefins[J]. Tetrahedron Letters,2006,47:287-289.
[41]Taylor Jason G,Whittall Neil,Hii King Kuok. Copper(Ⅱ)-catalysed addition of O—H bonds to norbornene[J].Chemical Communications,2005,40:5103-5105.
[42]Oe Yohei,Ohta Tetsuo,Ito Yoshihiko. Ruthenium catalyzed addition reaction of carboxylic acid across olefins withoutβ-hydride elimination[J]. Chemical Communications,2004,35:1620-1621.
[43]Oe Yohei,Ohta Tetsuo,Ito Yoshihiko. Addition reaction of2-phenylbenzoic acid onto unactivated olefins catalyzed by Ru(Ⅱ)-xantphos catalysis[J]. Tetrahedron Letters,2010,51:2806-2809.
[44]Higashi Shoko,Takenaka,Hiroto Ito Yoshihiko,et al. Synthesis of Ru Cl2(xantphos)L(L=PPh3,P(OPh)3,DMSO)complexes,and their catalytic activity for the addition of carboxylic acids onto olefins[J]. Journal of Organometallic Chemistry,2015,791:46-50.
[45]Komeyama Kimihiro,Mieno Yasuhiro,Yukawa Syotaro,et al. Cationic iron-catalyzed addition of carboxylic acids to olefins[J]. Chemistry Letters,2007,36(6):752-753.
[46]Choi Jun-Chul,Kohno Kazufumi,Masuda Daisuke,et al.Iron-catalysed green synthesis of carboxylic esters by the intermolecular addition of carboxylic acids to alkenes[J].Chemical Communication,2008,39(25):777-779.
[47]Qin Xubo,Chen Changjun,Zhang Lingjuan,et al. Palladiumcatalyzed highly regioselective and stereoselective decarboxylative arylation of unactivated olefins with aryl carboxylic acids[J]. Tetrahedron,2017,73:2242-249.
[48]Perkowski Andrew J,Nicewicz David A. Direct catalytic anti-markovnikov addition of carboxylic acids to alkenes[J]. Journal of the American Chemical Society,2013,135(28):10334-10337.
[2]林中祥,欧文华.微波辐射下莰烯与羧酸加成反应的研究[J].林产化学与工业,2004,24:41-46.Lin Zhongxiang,Ou Wenhua. Study on addition reaction between camphene and formic acid under microwave irradiation[J]. Chemistry and Industry of Forest Products,2004,24:41-46.
[3]Li Z,Zhang J,Brouwer C,et al. Brnsted acid catalyzed addition of phenols,carboxylic acids,and tosylamides to simple olefins[J]. Organic Letter,2006,8:4175-4178.
[4]Rosenfeld D C,Shekhar S,Takemiya A,et al. Hydroamination and hydroalkoxylation catalyzed by triflic acid. Parallels to reactions initiated with metal triflates[J]. Organic Letter,2006,8:4179-4182.
[5]Wang Bo,Gu Yanlong,Yang Liming,et al. Sulfamic acid as a green,efficient,recyclable and reusable catalyst for direct addition of aliphatic acid with cyclic olefins[J]. Catalysis Letters,2004,96:71-74.
[6]Dijs Ivo J,van Ochten Huibert L F,van Walree Cornelis A,et al. Alkyl sulphonic acid surface-functionalised silica as heterogeneous acid catalyst in the solvent-free liquidphase addition of acetic acid to camphene[J]. Journal of Molecular Catalysis A:Chemical,2002,188:209-224.
[7]Machadoa J,Castanheirob J E,Matosa Iet al. SBA-15 with sulfonic acid groups as a Green Catalyst for the acetoxylation ofα-pinene[J]. Microporous and Mesoporous Materials,2012,163:237-242.
[8]Zhou Feng,Tang Jihai,Fei Zhaoyang,et al. Efficient cyclohexyl acrylate production by direct addition of acrylic acid and cyclohexene over SBA-15-SO3H[J]. Journal of Porous Materials,2014,21:149-155.
[9]Gelbard Georges. Organic synthesis by catalysis with ionexchange resins[J]. Industrial&Engineering Chemistry Research,2005,44:8468-8498.
[10]Dijs Ivo J,van Ochten Huibert L F,van der Heijden Alwies J M,et al. The catalytic performance of sulphonated crosslinked polystyrene beads in the formation of isobornyl acetate[J]. Applied Catalysis A:General,2003,241:185-203.
[11]Zheng Huidong,Yan Zhongyi,Chu Shijiao,et al. Continuous synthesis of isobornyl acetate catalyzed by a strong acid cation exchange resin in an oscillatory flow reactor[J].Chemical Engineering&Processing:Process Intensification,2018,134:1-8.
[12]杨焕欣,杜长海,朱敏亮,等.阳离子交换树脂催化1-丁烯合成醋酸仲丁酯[J].化学工程师,2009,12:4-6.Yang Huanxin,Du Changhai,Zhu Minliang,et al. Synthesis of sec-butyl acetate catalyzed by strong acid cation exchange resin[J]. Chemical Engineer,2009,12:4-6.
[13]朱敏亮,徐平,杜长海.改性离子交换树脂催化合成醋酸仲丁酯[J].化学工程师,2007,3:13-15.Zhu Minliang,Xu Ping,Du Changhai. Synthesis of secbutyl acetate catalyzed by modified strong acid cation ion exchange resin[J]. Chemical Engineer,2007,3:13-15.
[14]许燕,汤吉海,崔咪芬,等.树脂催化甲基丙烯酸与环己烯反应合成甲基丙烯酸环己酯[J].石油化工,2011,40(10):1042-1045.Xu Yan,Tang Jihai,Cui Mifen,et al. Synthesis of cyclohexyl methacrylate from methacrylic acid and cyclohexene over resin catalyst synthesis of cyclohexyl methacrylate from methacrylic acid and cyclohexene over resin catalyst[J].Petrochemical Technology,2011,40(10):1042-1045.
[15]汤吉海,许燕,周峰,等.阳离子交换树脂催化合成丙烯酸环己酯[J].现代化工,2011,31(8):57-60.Tang Jihai,Xu Yan,Zhou Feng,et al. Synthesis of cyclohexyl acrylate with cation exchange resin as catalyst[J]. Modern Chemical Industry,2011,31(8):57-60.
[16]Yadav G D,Goel P K. Selective synthesis of perfumery grade cyclohexyl esters from cyclohexene and carboxylic acids over ion exchange resins:an example of 100%atom economy[J]. Green Chemistry,2000,2:71-78.
[17]Alexandre Demolis,Marion Eternot,Nadine Essayem,et al.New insights into the reactivity of biomass with butenes for the synthesis of butyl levulinates[J]. Chem Sus Chem,2017,10:2612-2617.
[18]Zhang Zhijun,Wang Qingwen,Yang Xulai,et al. Sulfonic acid resin-catalyzed addition of phenols,carboxylic acids,and water to olefins:model reactions for catalytic upgrading of bio-oil[J]. Bioresource Technology,2010,101:3685-3695.
[19]高文艺.磷铝杂原子固体酸催化剂催化合成乙酸异丙酯[J].精细石油化工进展,2003,4(12):30-31.Gao Wenyi. Catalytic Synthesis of isopropyl acetate using heteroatom-containing aluminophosphate solid acid catalyst[J]. Advances in Fine Petrochemicals,2003,4(12):30-31.
[20]王莉,魏民. Cs2. 5H0. 5PW12O40/Si O2催化剂上乙酸与烯烃酯化反应研究[J].化学与黏合,2006,28(2):94-96.Wang Li,Wei Min. Esterification of acetic acid and olefin over Cs2. 5H0. 5PW12O40/Si O2catalyst[J] Chemistry and Adhesion,2006,28(2):94-96.
[21]宋旭春,李萍,张起凯,等.固载杂多酸催化丁烯-1与乙酸合成乙酸丁酯[J].抚顺石油学院学报,2001,21(1):8-11.Song Xuchun,Li Ping,Zhang Qikai,et al. Synthesis ofbutyl acetate catalyzed by heteropolyacid catalyst supported on activated carbon[J]. Journal of Fushun Petroleum Institute,2001,21(1):8-11.
[22]杜长海,刘莹红,宋蓓蓓,等.磷钨酸催化混合C4合成醋酸仲丁酯[J].精细化工,2009,26(4):376-379.Du Changha,Liu Yinghong,Song Beibei,et al. Synthesis of sec-butyl acetate from mixed C4using the catalyst of phosphotungstic acid[J]. Fine Chemical,2009,26(4):376-379.
[23]徐平,金冲,杜长海.磷钨杂多酸催化合成醋酸仲丁酯[J].化学与生物工程,2007,24(12):22-24.Xu Ping,Jin Chong,Du Changhai. Synthesis of sec-butylacetate catalyzed by 12-tungst rophosphoric acid[J].Chemistry&Bioengineering,2007,24(12):22-24.
[24]李琴,柳云骐,周永敏,等.负载型杂多酸催化2-丁烯与醋酸直接酯化[J].石油化工,2007,36(12):1220-1224.Li Qin,Liu Yunqi,Zhou Yongmin,et al. Esterification of2-butylene with acetic acid catalyzed by silica-supported heteropolyacid[J]. Petrochemical Technology,2007,36(12):1220-1224.
[25]de Meireles Augusto L P,da Silva Rocha Kelly A,Ivan V Kozhevnikov,et al. Esterification of camphene over heterogeneous heteropoly acid catalysts:synthesis of isobornyl carboxylates[J]. Applied Catalysis A:General,2011,409-410:82-86.
[26]Robles-Dutenhefner Patricia A,da Silva Kelly A,Siddiqui M Rafiq H,et al. Hydration and acetoxylation of monoterpenes catalyzed by heteropoly acid[J]. Journal of Molecular Catalysis A:Chemical,2001,175:33-42.
[27]Yamamoto Yoshimi,Hatanaka Shigeru,Tsuji Katsuyuki,et al. Direct addition of acetic acid to ethylene to form ethyl acetate in the presence of H4Si W12O40/Si O2[J]. Applied Catalysis A:General,2008,344:55-60.
[28]Gu Yanlong,Shi Feng,Deng Youquan. Esterification of aliphatic acids with olefin promoted by Brnsted acidic ionic liquids[J]. Journal of Molecular Catalysis A:Chemical,2004,212:71-75.
[29]Duan Zhiying,Gu Yanlong,Zhang Juan,et al. Protic pyridinium ionic liquids:synthesis,acidity determination and their performances for acid catalysis[J]. Journal of Molecular Catalysis A:Chemical,2006,250:163-168.
[30]Liu Shiwei,Xie Congxia,Yu Shitao,et al. Esterification ofα-pinene and acetic acid using acidic ionic liquids as catalysts[J]. Catalysis Communications,2008,9:1634-1638.
[31]Gainsford Graeme J,Hosie Camila F,Weston Roderick J.Conversion ofα-pinene to terpinyl acetate over H-beta zeolites[J]. Applied Catalysis A:General,2001,209(1/2):269-277.
[32]Castanheiro J E,Fonseca I M,Ramos A M,et al. Acetoxylation of camphene catalysed by beta zeolite[J]. Catalysis Communications,2008,9:2205-2208.
[33]Yadav Mukesh Kr,Patil Mallikarjun V,Jasra Raksh V.Acetoxylation and hydration of limonene andα-pinene using cation-exchanged zeolite beta[J]. Journal of Molecular Catalysis A:Chemical,2009,297:101-109.
[34]Horiuchi C,Fukushima Tomoaki,Furuta Noriyuki,et al.Esterification of alkene with cerium(Ⅳ)sulfate in carboxylic acid[J]. Journal of Chemical Research,2003,(S):270-272.
[35]Essayem N,Martin V,Riondel A,et al. Esterification of acrylic acid with but-1-ene over sulfated Fe-and Mn-promoted zirconia[J]. Applied Catalysis A:General,2007,326:74-81.
[36]Yang Caiguang,He Chuan. Gold(Ⅰ)-catalyzed intermolecular addition of phenols and carboxylic acids to olefins[J]. Journal of the American Chemical Society,2005,127(19):6966-6967.
[37]Li Zigang,Zhang Junliang,Brouwer Chad,et al. Brnsted acid catalyzed addition of phenols,carboxylic acids,and tosylamides to simple olefins[J]. Organic Letters,2006,8(19):4175-4178.
[38]Yang Caiguang,Reich Nicholas W,Shi Zhangjie,et al.Intramolecular Additions of alcohols and carboxylic acids to inert olefins catalyzed by silver(Ⅰ)triflate[J]. Organic Letters,2005,7(21):4553-4556.
[39]Adrio Luis A,Quek Louisa Shuyi,Taylor Jason G,et al.Copper-catalysed intramolecular O-H addition to unactivated alkenes[J]. Tetrahedron,2009,65:10334-10338.
[40]Weiwer Michel,Dunach Elisabet. Indium(Ⅲ)-catalysed highly regioselective addition of thiolacetic acid to non-activated olefins[J]. Tetrahedron Letters,2006,47:287-289.
[41]Taylor Jason G,Whittall Neil,Hii King Kuok. Copper(Ⅱ)-catalysed addition of O—H bonds to norbornene[J].Chemical Communications,2005,40:5103-5105.
[42]Oe Yohei,Ohta Tetsuo,Ito Yoshihiko. Ruthenium catalyzed addition reaction of carboxylic acid across olefins withoutβ-hydride elimination[J]. Chemical Communications,2004,35:1620-1621.
[43]Oe Yohei,Ohta Tetsuo,Ito Yoshihiko. Addition reaction of2-phenylbenzoic acid onto unactivated olefins catalyzed by Ru(Ⅱ)-xantphos catalysis[J]. Tetrahedron Letters,2010,51:2806-2809.
[44]Higashi Shoko,Takenaka,Hiroto Ito Yoshihiko,et al. Synthesis of Ru Cl2(xantphos)L(L=PPh3,P(OPh)3,DMSO)complexes,and their catalytic activity for the addition of carboxylic acids onto olefins[J]. Journal of Organometallic Chemistry,2015,791:46-50.
[45]Komeyama Kimihiro,Mieno Yasuhiro,Yukawa Syotaro,et al. Cationic iron-catalyzed addition of carboxylic acids to olefins[J]. Chemistry Letters,2007,36(6):752-753.
[46]Choi Jun-Chul,Kohno Kazufumi,Masuda Daisuke,et al.Iron-catalysed green synthesis of carboxylic esters by the intermolecular addition of carboxylic acids to alkenes[J].Chemical Communication,2008,39(25):777-779.
[47]Qin Xubo,Chen Changjun,Zhang Lingjuan,et al. Palladiumcatalyzed highly regioselective and stereoselective decarboxylative arylation of unactivated olefins with aryl carboxylic acids[J]. Tetrahedron,2017,73:2242-249.
[48]Perkowski Andrew J,Nicewicz David A. Direct catalytic anti-markovnikov addition of carboxylic acids to alkenes[J]. Journal of the American Chemical Society,2013,135(28):10334-10337.