Tandem Palladium-Catalyzed 6- exo- dig Oxocyclization Coupling of δ-Acetylenic β-Ketoesters with Aryl Bromides and Chlorides: Route to Substituted Dihydropyrans.
Kołodziejczyk, Agata; Domański, Sylwester; Chaładaj, Wojciech; The Journal of organic chemistry 83 (2018) 12887–12896; doi:10.1021/acs.joc.8b01832

data_4035395
_publ_section_title
;
 Tandem Palladium-Catalyzed 6- exo- dig Oxocyclization Coupling of
 \d-Acetylenic \b-Ketoesters with Aryl Bromides and Chlorides: Route to
 Substituted Dihydropyrans.
;
_journal_issue                   20
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12887
_journal_page_last               12896
_journal_paper_doi               10.1021/acs.joc.8b01832
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C18 H19 N O3'
_chemical_formula_sum            'C18 H19 N O3'
_chemical_formula_weight         297.34
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                99.218(9)
_cell_angle_beta                 98.769(10)
_cell_angle_gamma                107.339(10)
_cell_formula_units_Z            4
_cell_length_a                   9.8898(17)
_cell_length_b                   11.4182(19)
_cell_length_c                   15.179(2)
_cell_measurement_reflns_used    3169
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      66.59
_cell_measurement_theta_min      3.02
_cell_volume                     1578.2(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.942
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0904
_diffrn_reflns_av_unetI/netI     0.0745
_diffrn_reflns_Laue_measured_fraction_full 0.942
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_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            31228
_diffrn_reflns_point_group_measured_fraction_full 0.942
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.594
_diffrn_reflns_theta_min         3.018
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.688
_exptl_absorpt_correction_T_max  0.9190
_exptl_absorpt_correction_T_min  0.8080
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.324
_exptl_crystal_size_mid          0.126
_exptl_crystal_size_min          0.125
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_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.0029(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     408
_refine_ls_number_reflns         5382
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.1279
_refine_ls_R_factor_gt           0.0736
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0921P)^2^+1.5292P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1956
_refine_ls_wR_factor_ref         0.2365
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3169
_reflns_number_total             5382
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01832_si_002.cif
_cod_data_source_block           KOL_01_0m
_cod_database_code               4035395
_shelx_estimated_absorpt_t_min   0.808
_shelx_estimated_absorpt_t_max   0.919
_shelxl_version_number           2014-3
_shelx_res_checksum              41069
_shelx_hkl_checksum              76478