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1. 发明申请

WO2003048033A3 MAGNESIUM MEDIATED PREPARATION OF FLUORINATED ALKYLSILANES 审中-公开
公开(公告)号：WO2003048033A3
公开(公告)日：2003-06-12
申请号：PCT/US2002/038127
申请日：2002-11-27
申请人： UNIVERSITY OF SOUTHERN CALIFORNIA , PRAKASH, Surya, G., K. , HU, Jinbo , OLAH, George, A.
发明人： PRAKASH, Surya, G., K. , HU, Jinbo , OLAH, George, A.
IPC分类号： C07F7/04
摘要： An efficient method is disclosed for the preparation of trifluoromethyl- and difluoromethylsilanes using magnesium metal mediated reductive tri- and difluoromethylation of chlorosilanes with tri- and difluoromethy sulfides, sulfoxides, and sulfones. One byproduct of the process is diphenyl disulfide. Since phenyl trifluoromethyl sulfone, sulfoxide and sulfide are readily prepared from readily available trifluoromethane and diphenyl disulfide, the method can be considered "pseudo-catalytic" for the preparation of (trifluoromethyl)trimethylsilane from environmentally benign trifluoromethane.

2. 发明申请

WO2005097739A3 NUCLEOPHILIC SUBSTITUTION REACTIONS OF DIFLUOROMETHYL PHENYL SULFONE WITH ALKYL HALIDES LEADING TO THE FACILE SYNTHESIS OF TERMINAL 1,1-DIFLUORO-1-ALKENES AND DIFLUOROMETHYLALKANES 审中-公开
标题翻译：二甲基甲硅烷基苯酚与烷基卤化物的引发反应合成终端1,1-二氟-1-烷基和二氟甲醛的合成
公开(公告)号：WO2005097739A3
公开(公告)日：2006-05-18
申请号：PCT/US2005010225
申请日：2005-03-25
申请人： UNIV SOUTHERN CALIFORNIA , PRAKASH G K SURYA , HU JINBO , OLAH GEORGE A , WANG YING
发明人： PRAKASH G K SURYA , HU JINBO , OLAH GEORGE A , WANG YING
IPC分类号： C07C319/02 , C07C17/361 , C07C41/18 , C07C43/225 , C07C45/90 , C07C315/04 , C07C317/14 , C07C317/18 , C07C319/08
CPC分类号： C07C43/225 , C07C17/361 , C07C41/18 , C07C315/04 , C07C22/08 , C07C317/14 , C07C317/18
摘要： (Benzenesulfonyl)difluoromethyl anion, in situ generated from difluoromethyl phenyl sulfone and a base, was found to easily undergo nucleophilic substitution reactions (S N 2 with primary alkyl halides, elemental halogens, and perfluoroalkyl halides with good selectivity. The formed (Benzenesulfonyl) difluoromethylalkanes are useful intermediates for the facile preparation of 1,1-difluoro-1alkenes and difluoromethylalkanes. Thus, difluoromethyl phenyl sulfone acts as both "CF 2 =" and CF 2 H" synthons.
摘要翻译：（苯磺酰基）二氟甲基阴离子，由二氟甲基苯基砜和碱原位产生，被发现容易进行亲核取代反应（具有主烷基卤，元素卤素和具有良好选择性的全氟烷基卤化物）形成的（苯磺酰基）二氟甲基烷烃是易于制备1,1-二氟-1-烯烃和二氟甲基烷烃的有用的中间体，因此二氟甲基苯基砜既可以作为“CF 2” 2 H“合成子。

3. 发明申请

WO2004063129A3 METHODS FOR NUCLEOPHILIC FLUOROMETHYLATION 审中-公开
标题翻译：用于核酸氟代甲基化的方法
公开(公告)号：WO2004063129A3
公开(公告)日：2004-12-29
申请号：PCT/US2004000651
申请日：2004-01-13
申请人： UNIV SOUTHERN CALIFORNIA , PRAKASH SURYA G K , HU JINBO , OLAH GEORGE A
发明人： PRAKASH SURYA G K , HU JINBO , OLAH GEORGE A
IPC分类号： C07C20060101 , C07C29/38 , C07C31/34 , C07C45/63 , C07C45/90 , C07C205/19 , C07C319/02 , C07C319/14 , C07C323/03 , C07D307/42
CPC分类号： C07D307/42 , C07C29/38 , C07C319/14 , C07C2603/74 , C07C323/03 , C07C33/46 , C07C31/38 , C07C35/52
摘要： A novel, convenient and efficient method for trifluoromethylation of substrate compounds is disclosed. Particularly, alkoxide and hydroxide induced nucleophilic trifluoromethylation of carbonyl compounds, disulfides and other electrophiles, using phenyl trifluoromethyl sulfone PhSO2CF3 (or sulfoxide PhSOCF3) is disclosed. A method of both symmetrical and unsymmetrical anti-2,2-difluoropropan-1,3-diols with high diastereoselectivity (up to 94 % de) is disclosed using dufluoromethyl phenyl sulfone. This unusual type of high diastereoselectivity was obtained via an intramolecular charge-charge repulsion effect rather than the traditional steric control (based on the Cram's rule). Thus, difluoromethyl phenyl sulfone can be used as a novel difluoromethylene dianion species (`CF2''), which can couple two electrophiles (such as diphenyl disulfide or non-enolizable aldehydes) to give new difluoromethylenated products.

4. 发明申请

WO2004063129A2 METHODS FOR NUCLEOPHILIC FLUOROMETHYLATION 审中-公开
标题翻译：用于核酸氟代甲基化的方法
公开(公告)号：WO2004063129A2
公开(公告)日：2004-07-29
申请号：PCT/US2004/000651
申请日：2004-01-13
申请人： UNIVERSITY OF SOUTHERN CALIFORNIA , PRAKASH, Surya, G., K. , HU, Jinbo , OLAH, George, A.
发明人： PRAKASH, Surya, G., K. , HU, Jinbo , OLAH, George, A.
IPC分类号： C07C
CPC分类号： C07D307/42 , C07C29/38 , C07C319/14 , C07C2603/74 , C07C323/03 , C07C33/46 , C07C31/38 , C07C35/52
摘要： A novel, convenient and efficient method for trifluoromethylation of substrate compounds is disclosed. Particularly, alkoxide and hydroxide induced nucleophilic trifluoromethylation of carbonyl compounds, disulfides and other electrophiles, using phenyl trifluoromethyl sulfone PhSO2CF3 (or sulfoxide PhSOCF3) is disclosed. A method of both symmetrical and unsymmetrical anti-2,2-difluoropropan-1,3-diols with high diastereoselectivity (up to 94 % de) is disclosed using dufluoromethyl phenyl sulfone. This unusual type of high diastereoselectivity was obtained via an intramolecular charge-charge repulsion effect rather than the traditional steric control (based on the Cram's rule). Thus, difluoromethyl phenyl sulfone can be used as a novel difluoromethylene dianion species (`CF2""), which can couple two electrophiles (such as diphenyl disulfide or non-enolizable aldehydes) to give new difluoromethylenated products.
摘要翻译：公开了一种用于底物化合物三氟甲基化的新颖，方便和有效的方法。特别地，公开了使用苯基三氟甲基砜PhSO 2 CF 3（或亚砜PhSOCF 3）的羰基化合物，二硫化物和其它亲电子体的醇盐和氢氧化物的亲核三氟甲基化。使用二氟甲基苯基砜公开了具有高非对映选择性（高达94％de）的对称和不对称的2,2-二氟丙-1,3-二醇的方法。这种不寻常类型的高非对映选择性通过分子内电荷 - 排斥效应而不是传统的空间控制获得（基于Cram的规则）。因此，二氟甲基苯基砜可以用作新的二氟亚甲基二阴离子物质（“CF2”“），其可以偶合两种亲电子试剂（例如二苯基二硫化物或不可烯化的醛）以产生新的二氟亚甲基化产物。

5. 发明申请

WO2005097739A2 NUCLEOPHILIC SUBSTITUTION REACTIONS OF DIFLUOROMETHYL PHENYL SULFONE WITH ALKYL HALIDES LEADING TO THE FACILE SYNTHESIS OF TERMINAL 1,1-DIFLUORO-1-ALKENES AND DIFLUOROMETHYLALKANES 审中-公开
标题翻译：二甲基甲硅烷基苯酚与烷基卤化物的引发反应合成终端1,1-二氟-1-烷基和二氟甲醛的合成
公开(公告)号：WO2005097739A2
公开(公告)日：2005-10-20
申请号：PCT/US2005/010225
申请日：2005-03-25
申请人： UNIVERSITY OF SOUTHERN CALIFORNIA , PRAKASH, G.K., Surya , HU, Jinbo , OLAH, George, A. , WANG, Ying
发明人： PRAKASH, G.K., Surya , HU, Jinbo , OLAH, George, A. , WANG, Ying
IPC分类号： C07C319/08
CPC分类号： C07C43/225 , C07C17/361 , C07C41/18 , C07C315/04 , C07C22/08 , C07C317/14 , C07C317/18
摘要： (Benzenesulfonyl)difluoromethyl anion, in situ generated from difluoromethyl phenyl sulfone and a base, was found to easily undergo nucleophilic substitution reactions (S N 2 with primary alkyl halides, elemental halogens, and perfluoroalkyl halides with good selectivity. The formed (Benzenesulfonyl) difluoromethylalkanes are useful intermediates for the facile preparation of 1,1-difluoro-1alkenes and difluoromethylalkanes. Thus, difluoromethyl phenyl sulfone acts as both “CF 2 =” and CF 2 H” synthons.
摘要翻译：（苯磺酰基）二氟甲基阴离子，由二氟甲基苯基砜和碱原位产生，被发现易于进行亲核取代反应（具有烷基卤化钠的SN2，元素卤素和具有良好选择性的全氟烷基卤化物）形成的（苯磺酰基）二氟甲基烷烃是有用的易于制备1,1-二氟-1-烯烃和二氟甲基烷烃的中间体，因此二氟甲基苯基砜既可以作为“CF2 =”和“CF2H”合成子。

6. 发明申请

WO03048033A2 MAGNESIUM MEDIATED PREPARATION OF FLUORINATED ALKYLSILANES 审中-公开
标题翻译：镁介导的氟化烷基硅烷的制备
公开(公告)号：WO03048033A2
公开(公告)日：2003-06-12
申请号：PCT/US0238127
申请日：2002-11-27
申请人： UNIV SOUTHERN CALIFORNIA , PRAKASH SURYA G K , HU JINBO , OLAH GEORGE A
发明人： PRAKASH SURYA G K , HU JINBO , OLAH GEORGE A
IPC分类号： C07F7/12 , C07F7/08 , C01B
CPC分类号： C07F7/0827
摘要： An efficient method is disclosed for the preparation of trifluoromethyl- and difluoromethylsilanes using magnesium metal mediated reductive tri- and difluoromethylation of chlorosilanes with tri- and difluoromethy sulfides, sulfoxides, and sulfones. One byproduct of the process is diphenyl disulfide. Since phenyl trifluoromethyl sulfone, sulfoxide and sulfide are readily prepared from readily available trifluoromethane and diphenyl disulfide, the method can be considered "pseudo-catalytic" for the preparation of (trifluoromethyl)trimethylsilane from environmentally benign trifluoromethane.
摘要翻译：公开了一种使用镁金属介导的氯硅烷与三氟甲磺酸和二氟甲硫基，亚砜和砜的还原性三氟甲基化和二氟甲基化制备三氟甲基和二氟甲基硅烷的有效方法。该方法的一个副产物是二苯基二硫化物。由于苯基三氟甲基砜，亚砜和硫化物容易由容易得到的三氟甲烷和二苯基二硫化物制备，所以该方法可以被认为是用于从环境友好的三氟甲烷制备（三氟甲基）三甲基硅烷的“假催化”。

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