Cu(OTf)(2)-Catalyzed Synthesis of 2,3-Disubstituted Indoles and 2,4,5-Trisubstituted Pyrroles from α-Diazoketones.
Reddy, B. V. Subba; Reddy, M. Ramana; Rao, Y. Gopal; Yadav, J. S.; Sridhar, B.; Organic letters 15 (2013) 464–467; doi:10.1021/ol303206w

data_1508860
_publ_section_title
;
 Cu(OTf)(2)-Catalyzed Synthesis of 2,3-Disubstituted Indoles and
 2,4,5-Trisubstituted Pyrroles from \a-Diazoketones.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              464
_journal_page_last               467
_journal_paper_doi               10.1021/ol303206w
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C14 H15 N O2'
_chemical_formula_sum            'C14 H15 N O2'
_chemical_formula_weight         229.27
_chemical_name_systematic
; 
ethyl 2-methyl-5-phenyl-1H-pyrrole-3-carboxylate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.883(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.7298(8)
_cell_length_b                   9.2723(6)
_cell_length_c                   11.8853(8)
_cell_measurement_reflns_used    5010
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      26.39
_cell_measurement_theta_min      2.80
_cell_volume                     1254.91(15)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1990)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_method       '\w scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_sigmaI/netI    0.0168
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11655
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.19
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.131
_refine_diff_density_min         -0.119
_refine_diff_density_rms         0.028
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         2198
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0396
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0647P)^2^+0.1862P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1124
_refine_ls_wR_factor_ref         0.1193
_reflns_number_gt                1862
_reflns_number_total             2198
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ol303206w_si_002.cif
_cod_data_source_block           an35m
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1508860