[ { "id": "authors:tn7tr-6dy56", "collection": "authors", "collection_id": "tn7tr-6dy56", "cite_using_url": "https://resolver.caltech.edu/CaltechAUTHORS:20190318-073543823", "type": "conference_item", "title": "Nucleophilic substitution reactions: A radical alternative to SN_1 and SN_2 reactions", "author": [ { "family_name": "Fu", "given_name": "Gregory Chung-Wei", "orcid": "0000-0002-0927-680X", "clpid": "Fu-G-C" } ], "abstract": "Classical methods for achieving nucleophilic substitutions of alkyl electrophiles (SN_1 and SN_2) have limited scope and are not generally amenable to enantioselective variants that employ readily available racemic electrophiles. In this\npresentation, we will describe how the combination of radical chem. and transition-metal catalysis has opened the door to addressing the challenges of reactivity and of enantioselectivity in nucleophilic substitution reactions of secondary and tertiary alkyl electrophiles.", "publisher": "Caltech Library", "publication_date": "2019-04" }, { "id": "authors:w8vbn-5q735", "collection": "authors", "collection_id": "w8vbn-5q735", "cite_using_url": "https://resolver.caltech.edu/CaltechAUTHORS:20180413-142635264", "type": "conference_item", "title": "Award Address (Herbert C. Brown Award for Creative Research in Synthetic Methods sponsored by the Purdue Borane Research Fund and the Herbert C. Brown Award Endowment). Nucleophilic substitution reactions: A radical alternative to S_N1 and S_N2 reactions", "author": [ { "family_name": "Fu", "given_name": "Gregory C.", "orcid": "0000-0002-0927-680X", "clpid": "Fu-G-C" } ], "abstract": "Classical methods for achieving nucleophilic substitutions of alkyl electrophiles (S_N1 and S_N2) have limited scope and are not\ngenerally amenable to enantioselective variants that employ readily available racemic electrophiles. In this presentation, we will\ndescribe how the combination of radical chem. and transition-metal catalysis has opened the door to addressing the challenges\nof reactivity and of enantioselectivity in nucleophilic substitution reactions of secondary and tertiary alkyl electrophiles.", "publisher": "Caltech Library", "publication_date": "2018-03" }, { "id": "authors:713kv-mq863", "collection": "authors", "collection_id": "713kv-mq863", "cite_using_url": "https://resolver.caltech.edu/CaltechAUTHORS:20170913-083924596", "type": "conference_item", "title": "Catalytic asymmetric synthesis of alkylsilanes enabled by stereoconvergent nickel-catalyzed cross-coupling", "author": [ { "family_name": "Schwarzwalder", "given_name": "Gregg", "clpid": "Schwarzwalder-G" }, { "family_name": "Fu", "given_name": "Gregory", "orcid": "0000-0002-0927-680X", "clpid": "Fu-G-C" } ], "abstract": "Over the years, the Fu group has demonstrated enantioconvergent cross-coupling reactions to be powerful\ntools for the synthesis of chiral mols. Most often, racemic secondary alkyl halide electrophiles are coupled with\nachiral nucleophiles to produce tertiary stereogenic centers in high yield and enantiomeric excess. In this talk, I will discuss our recent application of enantioconvergent nickel catalysis towards the prepn. of unactivated chiral alkyl silanes. The scope and limitations of this approach will be discussed, as well as some further applications of the enantioenriched products.", "publisher": "Caltech Library", "publication_date": "2017-08" }, { "id": "authors:gf680-cy417", "collection": "authors", "collection_id": "gf680-cy417", "cite_using_url": "https://resolver.caltech.edu/CaltechAUTHORS:20170503-101947409", "type": "conference_item", "title": "Metal-catalyzed cross-coupling reactions of alkyl electrophiles", "author": [ { "family_name": "Fu", "given_name": "Gregory C.", "orcid": "0000-0002-0927-680X", "clpid": "Fu-G-C" } ], "abstract": "Despite the tremendous accomplishments that have been described in the development of transition metal-catalyzed\ncoupling processes, it is nevertheless true that many significant opportunities remain. For example, to date the overwhelming majority of studies have focused on couplings between two sp -hybridized reaction sites (e.g., an aryl metal with an aryl halide). As of 2001, there were relatively few examples of metal-catalyzed coupling reactions of alkyl electrophiles. During the past decade, we have pursued the discovery of transition metal-based catalysts for coupling activated and unactivated alkyl\nelectrophiles that bear \u03b2 hydrogens. Our recent efforts to develop broadly applicable methods, including enantioselective processes, will be discussed.", "publisher": "Caltech Library", "publication_date": "2017-04" }, { "id": "authors:3b6sm-fn469", "collection": "authors", "collection_id": "3b6sm-fn469", "cite_using_url": "https://resolver.caltech.edu/CaltechAUTHORS:20160407-124341537", "type": "conference_item", "title": "Metal-catalyzed cross-coupling reactions of alkyl electrophiles", "author": [ { "family_name": "Fu", "given_name": "Gregory C.", "orcid": "0000-0002-0927-680X", "clpid": "Fu-G-C" } ], "abstract": "Despite the tremendous accomplishments that have been described in the development of transition metal- catalyzed\ncoupling processes, it is nevertheless true that many significant opportunities remain. For example, to date the overwhelming\nmajority of studies have focused on couplings between two sp - hybridized reaction sites (e.g., an aryl metal with an aryl\nhalide) . As of 2001, there were relatively few examples of metal- catalyzed coupling reactions of alkyl electrophiles.\nDuring the past decade, we have pursued the discovery of transition metal- based catalysts for coupling activated and\nunactivated alkyl electrophiles that bear \u03b2 hydrogens. Our recent efforts to develop broadly applicable methods, including\nenantioselective processes, will be discussed.", "publisher": "Caltech Library", "publication_date": "2016-03" }, { "id": "authors:cetsj-nd083", "collection": "authors", "collection_id": "cetsj-nd083", "cite_using_url": "https://resolver.caltech.edu/CaltechAUTHORS:20160302-081446965", "type": "conference_item", "title": "Mechanistic insights into photo-induced, copper-catalyzed alkylations of amines", "author": [ { "family_name": "Ahn", "given_name": "Jun Myun", "clpid": "Ahn-Jun-Myun" }, { "family_name": "Hannoun", "given_name": "Kareem", "orcid": "0000-0003-3176-1104", "clpid": "Hannoun-Kareem-I" }, { "family_name": "Ratani", "given_name": "Tanvi", "clpid": "Ratani-Tanvi-S" }, { "family_name": "Creutz", "given_name": "Sidney", "orcid": "0000-0003-4440-5336", "clpid": "Creutz-Sidney-E" }, { "family_name": "Peters", "given_name": "Jonas C.", "orcid": "0000-0002-6610-4414", "clpid": "Peters-J-C" }, { "family_name": "Fu", "given_name": "Gregory C.", "orcid": "0000-0002-0927-680X", "clpid": "Fu-G-C" } ], "abstract": "Photoinduced, copper-catalyzed cross-couplings have emerged as an attractive class of lightdriven\ntransformations to construct carbon-nitrogen bonds in recent years. Despite the\nbroadening scope with respect to coupling partners, the understanding of the operating\nmechanisms has been limited to date. Herein, a mechanistic investigation of a photoinduced,\ncopper-catalyzed cross-coupling of amines and alkyl halides, including spectroscopic evidence\nfor a copper intermediate, is presented.", "publisher": "Caltech Library", "publication_date": "2015-11" }, { "id": "authors:r9fw4-0zg75", "collection": "authors", "collection_id": "r9fw4-0zg75", "cite_using_url": "https://resolver.caltech.edu/CaltechAUTHORS:20150408-081923612", "type": "conference_item", "title": "Metal-catalyzed cross-coupling reactions of alkyl electrophiles", "author": [ { "family_name": "Fu", "given_name": "Gregory C.", "orcid": "0000-0002-0927-680X", "clpid": "Fu-G-C" } ], "abstract": "Despite the tremendous accomplishments that have been described in the development of transition metal-catalyzed\ncoupling processes, it is nevertheless true that many significant opportunities remain. For example,\nto date the overwhelming majority of studies have focused on couplings between two sp2-hybridized reaction\nsites (e.g., an aryl metal with an aryl halide). As of 2001, there were relatively few examples of metalcatalyzed\ncoupling reactions of alkyl electrophiles. During the past decade, we have pursued the\ndiscovery of transition metal-based catalysts for coupling activated and unactivated alkyl electrophiles that\nbear b hydrogens. Our recent efforts to develop broadly applicable methods, including enantioselective\nprocesses, will be discussed.", "publisher": "American Chemical Society", "publication_date": "2015-03" }, { "id": "authors:fzagm-4mb43", "collection": "authors", "collection_id": "fzagm-4mb43", "cite_using_url": "https://resolver.caltech.edu/CaltechAUTHORS:20140812-105957073", "type": "conference_item", "title": "Catalytic cross-coupling with copper and light", "author": [ { "family_name": "Peters", "given_name": "Jonas C.", "orcid": "0000-0002-6610-4414", "clpid": "Peters-J-C" }, { "family_name": "Fu", "given_name": "Gregory", "orcid": "0000-0002-0927-680X", "clpid": "Fu-G-C" } ], "abstract": "Carbon-nitrogen bond-forming reactions of amines with aryl halides to generate arylamines (anilines), mediated by a stoichiometric copper reagent at elevated temp. (>180 \u00b0C), were first described by Ullmann in 1903. Recent advances in catalytic Ullmann-type cross-couplings make these bond-forming processes powerful tools for org. synthesis. In this talk I will describe a recent collaborative effort between the Fu and Peters research groups at Caltech to develop photo-induced, copper-catalyzed C-X cross-couplings (X = N, S, O, C) as a methodolgically simple, mild approach to Ullmann-type bond constructions.", "publisher": "Caltech Library", "publication_date": "2014-08" } ]