Heteroaromatics: The Mal Synthesis of Clausevatine D

2013 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Carboxylic Acids ◽  
South China ◽  
University Of Illinois ◽  
Dicarbonyl Compound ◽  
Furoic Acid ◽  
University Of Technology ◽  
Decarboxylative Coupling ◽  
National University ◽  
La Jolla ◽  
The University

Huanfeng Jiang of the South China University of Technology showed (J. Org. Chem. 2010, 75, 966) that an alkynoate 1 could be condensed with a 1,3-dicarbonyl compound 2 to give, under oxidizing conditions, the furan 3. Phil Ho Lee of Kangwon National University found (Tetrahedron Lett. 2010, 51, 1899) that the enyne 4 cyclized smoothly to the furan 5. Yahong Li of Suzhou University and Vladimir Gevorgyan of the University of Illinois, Chicago, demonstrated (J. Am. Chem. Soc. 2010, 132, 7645) that the cyclization of 6 proceeded with silyl migration, to give 7. François Bilodeau and Pat Forgione of Boehringer Ingelheim (Canada) optimized (J. Org. Chem. 2010, 75, 1550) the Pd-mediated decarboxylative coupling of a furoic acid 8 with 9 to give 10. This protocol also worked well with pyrrole carboxylic acids. In another transformation of a preformed pyrrole, Masatomo Iwao of Nagasaki University observed (Organic Lett. 2010, 12, 2734) that in the presence of LDA/diisopropylamine, the initially formed 2-anion from the deprotonation of 11 gave the 2-product 12 with more reactive electrophiles but the 5-product 13 with less reactive electrophiles. Umasish Jana of Jadavpur University developed (J. Org. Chem. 2010, 75, 1674) a route to more highly substituted pyrroles such as 17 using the remarkable four-component coupling of 14, 15, and 16 with nitromethane, the carbon of which was incorporated in the product. Laura L. Anderson, also of the University of Illinois, Chicago, designed (Organic Lett. 2010, 12, 2290) a clever approach to pyrroles, based on the Ir-catalyzed rearrangement of O-allyl oximes such as 18. Xiaofeng Tong of the East China University of Science and Technology reported (Chem. Commun. 2010, 312) the condensation of 20 with 21 to give the dihydropyridine 22. Base-mediated elimination of sulfinate could convert 22 into the pyridine. Jin-Quan Yu of Scripps/La Jolla found (Angew. Chem. Int. Ed. 2010, 49, 1275) that Pd-mediated activation of the nictotinamide 23 proceeded with high regioselectivity, leading to 25. Zhiping Li of Remnin University of China demonstrated (J. Org. Chem. 2010, 75, 4636) that the chloroenamine 26 cyclized to the indole 27 on exposure to NaI.

Reactions of Alkenes

2013 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
South China ◽  
Diazonium Salt ◽  
Solvent Free ◽  
University Of California ◽  
University Of Wisconsin ◽  
University Of Technology ◽  
Complementary Approach ◽  
Re Catalyst ◽  
La Jolla ◽  
The University

Ana C. Fernandes of the Instituto Superior Técnico, Lisboa, devised (Tetrahedron Lett. 2010, 51, 1048) an effective Re catalyst for the solvent-free hydrogenation of an alkene 1. Yasushi Imada and Takeshi Naota of Osaka University showed (Organic Lett. 2010, 12, 32) that a flavin could catalyze the hydrogenation of an alkene 3. Note that the thioether was stable under these conditions. Huanfeng Jian of the South China University of Technology developed (J. Org. Chem. 2010, 75, 2321) a Pd-based protocol for the oxidative cleavage of an alkene 5. The cleavage could be halted at the cis diol. K. C. Nicolaou of Scripps/La Jolla optimized (Organic Lett. 2010, 12, 1552) a complemetary cleavage of an alkene 7, again proceeding via the diol. J. R. Falck of UT Southwestern established (J. Org. Chem. 2010, 75, 1701) the Heck-type oxidative silylation of an alkene 9 to the Z -silane 10. Timothy F. Jamison of MIT effected (Chem. Commun. 2010, 46, 907) the borylation of an alkene 11. Kálmán Szabó of Stockholm University reported (Angew. Chem. Int. Ed. 2010, 49, 4051) a complementary approach for effecting the same transformation. Cathleen M. Crudden of Queen’s University, Kingston, observed (J. Am. Chem. Soc. 2010, 132, 131) that Rh-catalyzed hydroboration of 13 delivered the borane 14. Tehshik P. Yoon of the University of Wisconsin used (J. Am. Chem. Soc. 2010, 132, 4570) Fe to catalyze the addition of an oxaziridine 16 to an alkene 15. Yasuhiro Shiraishi of Osaka University improved (J. Org. Chem. 2010, 75, 1450) the photochemical addition of acetone to an alkene 18. Chul-Ho Jun of Yonsei University described (Tetrahedron Lett. 2010, 51, 160) a related procedure. Professor Jamison effected (J. Am. Chem. Soc. 2010, 132, 6880) the branching homologation of an alkene to give 21 . F. Dean Toste of the University of California, Berkeley, accomplished (J. Am. Chem. Soc. 2010, 132, 8885) the oxidative homologation of an alkene to the ester 22. Markus R. Heinrich of the Universität Erlangen-Nürnberg developed (Tetrahedron Lett. 2010, 51, 1758) the tandem addition of the hydroperoxide 23 and a diazonium salt 24, leading to 25.

Advances in Organic Functional Group Transformation

2013 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Carboxylic Acids ◽  
Allyl Ether ◽  
Primary Alcohols ◽  
Ru Catalyst ◽  
University Of Technology ◽  
National University ◽  
Tokyo Institute ◽  
Institute Of Technology ◽  
The University ◽  
Technological University

There have been several significant advances in N-alkylation using alcohols. Matthias Beller of Universität Rostock devised (Angew. Chem. Int. Ed. 2010, 49, 8126) a Ru catalyst for the amination of secondary and benzylic primary alcohols with ammonia. Dieter Vogt of the Eindhoven University of Technology reported (Angew. Chem. Int. Ed. 2010, 49, 8130) related transformations. Pei-Qiang Huang of Xiamen University showed (Chem. Commun. 2010, 46, 7834) that debenzylation of 3 in methanol led to the N-methyl amine 4. Parallel results have been reported with Ir (J. Am. Chem. Soc. 2010, 132, 15108), Au (Chem. Eur. J. 2010, 16, 13965), and Cu (Chem. Lett. 2010, 39, 1182). Peter J. Scammells of Monash University found (J. Org. Chem. 2010, 75, 4806) that demethylation of an N-oxide could be effected with Fe powder. Yao Fu and Qingxiang Guo of the University of Science and Technology of China N-vinylated (Tet. Lett. 2010, 51, 5476) a sulfonamide 7 with vinyl acetate and a Pd catalyst. Acyl amides could also be N-vinylated under these conditions. Hirokazu Urabe of the Tokyo Institute of Technology reported (Org. Lett. 2010, 12, 4137) that the stereodefined secondary sulfonamide of 9 could be displaced by an internal nucleophile, to give the product 11 with inversion of absolute configuration. Teruo Umemoto of IM&T Research devised (J. Am. Chem. Soc. 2010, 132, 18199) the remarkable fluorinating agent 13. In addition to converting secondary alcohols to the corresponding fluorides and ketones to gem-difluorides, 13 cleanly converted the carboxylic acids of 12 to trifluoromethyl groups. Paul G. Williard of Brown University demonstrated (Org. Lett. 2010, 12, 5378) that LDA converted an allyl ether 15 specifically to the (Z)-propenyl ether 16. Phil Lee Ho of Kangwon National University and Sunggak Kim of Nanyang Technological University could add (Angew. Chem. Int. Ed. 2010, 49, 6806) a phosphate to an alkyne 17 to make either the less substituted or the more substituted enol phosphate. Professor Kim reported (J. Org. Chem. 2010, 75, 7928) similar results with the addition of carboxylic acids.

scholarly journals Back-end porting of FT_MX based on LLVM compilation architecture

2021 ◽  
Vol 336 ◽  
pp. 04018
Author(s):  
Ping Deng ◽  
Xiaolong Zhu ◽  
Haiyan Sun ◽  
Yi Ren
Keyword(s):  
Open Source ◽  
High Performance ◽  
Instruction Set ◽  
University Of Illinois ◽  
Specific Process ◽  
Defense Technology ◽  
Migration Mechanism ◽  
National University ◽  
Compiler Framework ◽  
The University

The processor FT_MX is a high-performance chip independently developed by the National University of Defense Technology, with an innovative architecture and instruction set. LLVM architecture is a widely used and efficient open source compiler framework initiated by the University of Illinois. This paper introduces the basic architecture and functions of LLVM, analyzes the back-end migration mechanism of the architecture in detail, and gives the specific process of implementing FT_MX back-end migration, and realizes the support of LLVM architecture to the back-end of FT_MX processor.

Preparation of Heteroaromatic Derivatives

2011 ◽  
Author(s):  
Douglass Taber
Keyword(s):  
Ring Expansion ◽  
University Of Pennsylvania ◽  
Au Catalyst ◽  
University Of Illinois ◽  
Oxidative Rearrangement ◽  
University Of Technology ◽  
Acidic Conditions ◽  
The University ◽  
École Polytechnique ◽  
Pais Vasco

Several new routes to furans and to pyrroles have recently been put forward. Inspired by the Achmatowicz ring expansion, Patrick J. Walsh of the University of Pennsylvania developed (J. Am. Chem. Soc. 2008, 130, 4097) the oxidative rearrangement of 3-hydrox-alkyl furans such as 1 to the 3-aldehyde 2. José M. Aurrecoechea of the Universidad del País Vasco established (J. Org. Chem. 2008, 73, 3650) that cumulated alcohols, available by reduction of alkynes such as 3 with SmI2, rearrange under Pd catalysis, and then add to an acceptor alkene such as 4, to give the furan 5. Vladimir Gevorgyan of the University of Illinois at Chicago used (J. Am. Chem. Soc. 2008, 130, 1440) an Au catalyst to rearrange an allene such as 6 to the bromo furan 7. Fabien L. Gagosz of the Ecole Polytechnique, Palaiseau, also found (Organic Lett. 2007, 9, 3181) that an Au catalyst rearranged the eneyne 8 to the pyrrole 9. Azido esters such as 10 are readily prepared from the corresponding aldehyde by phosphonate condensation. Shunsuke Chiba and Koichi Narasaka of Nanyang Technology University demonstrated (Organic Lett. 2008, 10, 313) that thermal condensation of 10 with acetyl acetone 11 gave the pyrrole 12, while Cu catalyzed condensation with acetoacetate 13 gave the complementary pyrrole 14. Huan-Feng Jiang of South China University of Technology observed (Tetrahedron Lett. 2008, 49, 3805) that condensation of an acid chloride 15 with an alkyne 16, presumably to give the alkynyl ketone, followed by the addition of hydrazine delivered the pyrazole 17. Masanobu Uchiyama of RIKEN and Florence Mongin of the Université de Rennes 1 established (J. Org. Chem. 2008, 73, 177) that a pre-formed pyrazole 18 could be metalated and then iodinated, to give 19. Xiaohu Deng of Johnson & Johnson, San Diego reported (Organic Lett. 2008, 10, 1307; J. Org. Chem. 2008, 73, 2412) complementary routes to pyrazoles, combining 20 and 21 under acidic conditions to give 22, and under basic conditions to give 23.

Synthesis of Substituted Benzenes: The Carter Synthesis of Siamenol

2011 ◽  
Author(s):  
Douglass Taber
Keyword(s):  
Aryl Halides ◽  
Substituted Benzenes ◽  
Diversity Oriented Synthesis ◽  
University Of Illinois ◽  
University Of Houston ◽  
Direct Functionalization ◽  
University Of Edinburgh ◽  
Aryl Tosylates ◽  
La Jolla ◽  
The University

Tosylates are among the least expensive, but also among the least reactive toward Pd(0) oxidative addition, of aryl sulfonates. Jie Wu of Fudan University has now devised conditions (J. Org. Chem. 2007, 72, 9346) for the Pd-catalyzed coupling of aryl tosylates such as 1 with arene trifluoroborates. Kei Manabe of RIKEN has found (Organic Lett. 2007, 9, 5593) that an ortho OH activates an adjacent Cl for Pd-mediated coupling, allowing the conversion of 4 to 6 . Philippe Uriac and Pierre van de Weghe of the Université de Rennes I have developed (Organic Lett. 2007, 9, 3623) conditions for the catalytic acylation of aryl halides with alkenyl acetates such as 8. Multi-component coupling lends itself well to diversity-oriented synthesis. As illustrated by the combination of 10 with 11 and 12 to give 13 reported (Organic Lett. 2007, 9, 5589) by Michael F. Greaney of the University of Edinburgh, benzynes can do double addition with high regiocontrol. For other recent references to unsymmetrical double additions to arynes, see Angew.Chem. Int. Ed. 2007, 46, 5921; Chem. Commun. 2007, 2405; and J. Am. Chem. Soc. 2006, 128, 14042. C-H functionalization of arenes is of increasing importance. John F. Hartwig of the University of Illinois has described (Organic Lett. 2007, 9, 757; 761) improved conditions for Ir-catalyzed meta borylation, and conditions for further coupling of the initial borate 16 to give amines such as 17. Lei Liu and Qing-Xiang Guo of the University of Science and Technology, Hefei have found (Tetrahedron Lett. 2007, 48, 5449) that oxygen can be used as the stoichiometric oxidant in the Pd-catalyzed functionalization of H’s ortho to anilides. Two other research groups (J. Am. Chem. Soc. 2007, 129, 6066; Angew. Chem. Int. Ed. 2007, 46, 5554; J. Org. Chem. 2007, 72, 7720) reported advances in this area. In a close competition, Jin-Quan Yu, now at Scripps/La Jolla (J. Am. Chem. Soc. 2007, 129, 3510) and Olafs Daugulis of the University of Houston (J. Am. Chem. Soc. 2007, 129, 9879) both reported that a carboxyl group can activate an ortho H for direct functionalization.

C–O Ring Construction: The Oger/Lee/Galano Synthesis of 7(RS)-ST-Δ8-11-dihomo-Isofuran

2017 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Ring Expansion ◽  
Radical Mechanism ◽  
Columbia University ◽  
University Of Michigan ◽  
Max Planck ◽  
University Of British Columbia ◽  
University Of Technology ◽  
National University ◽  
Seoul National University ◽  
The University

Shaorong Yang and Huanfeng Jiang of the South China University of Technology assembled (Angew. Chem. Int. Ed. 2014, 53, 7219) the β-lactone 3 by the Pd-catalyzed addition of 2 to the alkyne 1. Jack R. Norton of Columbia University observed (J. Am. Chem. Soc. 2015, 137, 1036) that the vanadium-mediated reduc­tive cyclization of 4 proceeded by a free radical mechanism, leading to the cis 3,4-disubstituted tetrahydrofuran 5. The cyclization of 6 to 7 developed (J. Org. Chem. 2015, 80, 965) by Glenn M. Sammis of the University of British Columbia also involved H atom transfer. Amy R. Howell of the University of Connecticut devised (J. Org. Chem. 2015, 80, 5196) the ring expansion of the β-lactone 8 to the tet­rahydrofuran 9. Dmitri V. Filippov and Jeroen D. C. Codée of Leiden University showed (J. Org. Chem. 2015, 80, 4553) that the net reductive alkylation of the lac­tone 10 led to 11 with high diastereocontrol. A. Stephen K. Hashmi of the Ruprecht-Karls-Universität Heidelberg optimized (Chem. Eur. J. 2015, 21, 427) the gold-mediated rearrangement of the ester 12 to the lactone 13. This reaction apparently proceeded by the coupling of the metalated lac­tone with a propargylic carbocationic species. Benjamin List of the Max-Planck-Institut für Kohlenforschung developed (Angew. Chem. Int. Ed. 2015, 54, 7703) an organocatalyst that mediated the addition of 15 to 14, leading to 16 in high ee. Scott E. Denmark of the University of Illinois published (Nature Chem. 2015, 6, 1056) a detailed study of the enantioselective cyclization of 17 to 18. Shunichi Hashimoto of Hokkaido University established (Tetrahedron Lett. 2015, 56, 1397) that his catalyst was effective for the cycli­zation of 19 to 20. Debendra K. Mohapatra of the Indian Institute of Chemical Technology showed (J. Org. Chem. 2015, 80, 1365) that allyl trimethylsilane could trap the intermediate from the cyclization of 21, leading to 22 with high diastereocontrol. Young-Ger Suh of Seoul National University used (Chem. Commun. 2015, 51, 9026) a Pd catalyst to cyclize 23 to (−)-deguelin 24. John Montgomery of the University of Michigan showed (Org. Lett. 2015, 17, 1493) that the Ni-catalyzed reduc­tive cyclization of 25 to 26 proceeded with high diastereoselectivity.

Reactions of Alkenes

2017 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Iron Catalyst ◽  
Catalytic Reduction ◽  
Indian Institute ◽  
Yale University ◽  
Terminal Alkene ◽  
National University ◽  
Institute Of Technology ◽  
La Jolla ◽  
The University

The catalytic reduction of the alkene 1 gave the cis-fused product (not illustrated), by kinetic H₂ addition to the less congested face of the alkene. Ryan A. Shenvi of Scripps La Jolla found (J. Am. Chem. Soc. 2014, 136, 1300) conditions for stepwise HAT, con­verting 1 to the thermodynamically-favored trans-fused ketone 2. Seth B. Herzon of Yale University devised (J. Am. Chem. Soc. 2014, 136, 6884) a protocol for the reduc­tion, mediated by 4, of the double bond of a haloalkene 3 to give the saturated halide 5. The Shenvi conditions also reduced a haloalkene to the saturated halide. Daniel J. Weix of the University of Rochester and Patrick L. Holland, also of Yale University, established (J. Am. Chem. Soc. 2014, 136, 945) conditions for the kinetic isomerization of a terminal alkene 6 to the Z internal alkene 7. Christoforos G. Kokotos of the University of Athens showed (J. Org. Chem. 2014, 79, 4270) that the ketone 9, used catalytically, markedly accelerated the Payne epoxidation of 8 to 10. Note that Helena M. C. Ferraz of the Universidade of São Paulo reported (Tetrahedron Lett. 2000, 41, 5021) several years ago that alkene epoxidation was also easily carried out with DMDO generated in situ from acetone and oxone. Theodore A. Betley of Harvard University prepared (Chem. Sci. 2014, 5, 1526) the allylic amine 12 by reacting the alkene 11 with 1-azidoadamantane in the presence of an iron catalyst. Rodney A. Fernandes of the Indian Institute of Technology Bombay developed (J. Org. Chem. 2014, 79, 5787) efficient conditions for the Wacker oxida­tion of a terminal alkene 6 to the methyl ketone 13. Yong-Qiang Wang of Northwest University oxidized (Org. Lett. 2014, 16, 1610) the alkene 6 to the enone 14. Peili Teo of the National University of Singapore devised (Chem. Commun. 2014, 50, 2608) conditions for the Markovnikov hydration of the alkene 6 to the alcohol 15. Internal alkenes were inert under these conditions, but Yoshikazo Kitano of the Tokyo University of Agriculture and Technology effected (Synthesis 2014, 46, 1455) the Markovnikov amination (not illustrated) of more highly substituted alkenes.

Benzene Derivatives: The Tanino-Miyashita Synthesis of Zoanthenol

2013 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Benzoic Acid ◽  
University Of Pennsylvania ◽  
University Of Southern California ◽  
Aryl Chlorides ◽  
National University ◽  
Rh Catalyst ◽  
Nitro Aromatics ◽  
La Jolla ◽  
University Of Oslo ◽  
The University

Yuqing Hou of Southern Illinois University found (J. Org. Chem. 2009, 74, 6362) that the peroxy ether 2 served effectively to directly transfer a methoxy group to the lithiated 1 to give 3. Wanzhi Chen of Zhejiang University, Xixi Campus, showed (J. Org. Chem. 2009, 74, 7203) that pyrimidines such as 4, readily prepared from the corresponding phenol, underwent smooth Pd-catalyzed ortho acetoxylation. Trond Vidar Hansen of the University of Oslo observed (Tetrahedron Lett. 2009, 50, 6339) that simple electrophilic formylation of phenols such as 6 also proceeded with high ortho selectivity. Kyung Woon Jung of the University of Southern California optimized (J. Org. Chem. 2009, 74, 6231) the Rh catalyst for ortho C-H insertion, converting 8 into 9. Jin-Quan Yu of Scripps/La Jolla devised (Science 2010, 327, 315) a protocol for carboxy-directed catalytic ortho palladation that allowed subsequent Heck coupling, transforming 10 into 11. Norikazu Miyoshi of the University of Tokushima established (Chem. Lett. 2009, 38, 996) that in situ generated strontium alkyls added 1,6 to benzoic acid 13, to give, after mild oxidative workup, the 4-alkyl benzoic acid 15. Amin Zarei of Islamic Azad University showed (Tetrahedron Lett. 2009, 50, 4443) that their previously developed protocol for preparing stable diazonium silica sulfates could be extended to the preparation of an aryl azide such as 17. Stephen L. Buchwald of MIT developed (J. Am. Chem. Soc. 2009, 131, 12898) a Pd-mediated protocol for the conversion of aryl chlorides to the corresponding nitro aromatics. Virgil Percec of the University of Pennsylvania has also reported (Organic Lett. 2009, 11, 4974) the conversion of an aryl chloride to the borane, and Guy C. Lloyd-Jones has described (Angew. Chem. Int. Ed. 2009, 48, 7612) the conversion of phenols to the corresponding thiols. Kwang Ho Song of Korea University and Sunwoo Lee of Chonnam National University demonstrated (J. Org. Chem. 2009, 74, 6358) that the Ni-mediated homologation of aryl halides worked with a variety of primary and secondary formamides. Kwangyong Park of Chung-Ang University observed (J. Org. Chem. 2009, 74, 9566) that Ni catalysts also mediated the coupling of Grignard reagents with the tosylate 22 not in the usual way but with the C-S bond to give 23.

Development of Flow Reactions

2015 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Flow Reactor ◽  
Flow System ◽  
Max Planck ◽  
Flow Reactors ◽  
University Of Technology ◽  
National University ◽  
Continuous Flow Reactors ◽  
Institute Of Technology ◽  
S Chandrasekhar ◽  
The University

For a review of a monograph by C. Wiles and P. Watts on applications of flow reactors in organic synthesis, see Org. Process. Res. Dev. 2011, 15, 947. For a review by Klavs S. Jensen of MIT of flow approaches, see Angew. Chem. Int. Ed. 2011, 50, 7502. Hans-René Bjørsvik of the University of Bergen described (Org. Process. Res. Dev. 2011, 15, 997) a multijet oscillating disc microreactor, and Andreas Schmid of the Technische Universität Dortmund (Adv. Synth. Catal. 2011, 353, 2511) and László Poppe of the Budapest University of Technology and Economics discussed (Adv. Synth. Catal. 2011, 353, 2481) continuous flow reactors for biotransformations. Gases are readily handled in a flow apparatus. S. Chandrasekhar of the Indian Institute of Chemical Technology, Hyderabad demonstrated (Tetrahedron Lett. 2011, 52, 3865) partial deuteration of 1 to 2, using D2O as the deuterium source. Peter H. Seeberger of the Max Planck Institute, Potsdam oxidized (Org. Lett. 2011, 13, 5008) 3 to 4 with singlet oxygen. Dong-Pyo Kim of Chungnam National University and Robert H. Grubbs of Caltech effected (Org. Lett. 2011, 13, 2398) ethenolysis of 5 to give 6 and 7. Takashi Takahashi of the Tokyo Institute of Technology showed (Chem. Commun. 2011, 47, 12661) that even phosgene could be handled in a flow system, using it to activate 8 for condensation with benzylamine to give 9. In the liquid phase, Stephen L. Buchwald of MIT prepared (Angew. Chem. Int. Ed. 2011, 50, 8900) 11 by the fluorination of 10. Jesús Alcázar of Janssen Pharmaceutical, Toledo, showed (Tetrahedron Lett. 2011, 52, 6058) that a nitrile 12 could be reduced in a flow system to the aldehyde 13. Mark York of CSIRO prepared (Tetrahedron Lett. 2011, 52, 6267) the furan 16 by condensation of 14 with 15. Floris P.J.T. Rutjes of Radboud University Nijmegen used (Org. Process Res. Dev. 2011, 15, 783) the careful controls of a flow reactor to optimize the exothermic combination of 17 with 18 to give 19. Professor Buchwald demonstrated (Angew. Chem. Int. Ed. 2011, 50, 10665) a flow protocol for the lithiation of 20 with in situ borylation and Pd-catalyzed coupling with 21 to give 22.

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